I’m a forty-two year old single woman that some might call a MILF. I never had much of a sexual appetite while raising the kids but, that is most probably due to my lame excuse of an ex-husband. Now that the kids are flying solo, I wanted to experiment in the bedroom, especially by trying anal sex at some point. I wanted to check that one off my sexual bucket list and be able to say that I was truly a try-sexual woman! For some reason, the one thing I wanted to do as soon the divorce papers were signed was to get fucked in the ass! Please don’t ask me why. . . I can’t explain it. Perhaps, it was during my sexual frustration stage I would search the web and download anal sex movies. There was something deep inside me where I just longed to watch anal sex while I masturbated.
I started dating a couple of months after the divorce and met a nice professional man that knew how to treat a lady but, as I found out, didn’t know how to really please a woman, if you know what I mean. One night, I was feeling playful and had my brand new Roku player set to watch anal sex movies all night long. I asked boyfriend, Andrew to come over for wine and some dinner, then hopefully a whole lot more! After an amazing dinner courtesy of me, I asked Andrew is he ever wanted to see anal sex? He looked rather shocked as up to this point, we had only kissed and petted a little.
Once the initial shock of my proposition subsided, I took my remote and hit up the dirtiest fucking anal sex movies I could find. “Now, we are ready to watch anal sex,” I proclaimed! I could tell Andrew was more than intrigued now. He said (in near can’t believe this is actually happening tone), “I always wanted to see anal sex but, now I get to watch anal sex with a hot babe like you.” I joked, “no need for trying to score brownie points, I’ve been waiting for this moment since my divorce! With that my favorite anal sex porn star, Riley Reid came on screen before cumming on screen. She is such a dirty little anal slut and I love it!
After watching Riley take some HUGE cocks up her sexy petite anus. I so thought I was ready for a cock in my ass but, fuck, did I ever regret tempting it that night! Neither Andrew or myself had ever partaken in anal sex before and didn’t fully realize the necessity of proper lubrication. Those porn stars make it look so fucking easy. I mean they take a fucking pounding and actually seem to get off while doing it. I certainly never thought I would ever see my favorite MILF, Cherie DeVille take a cock up the ass but, it sure looks like she enjoys it now! I stood up and told Andrew to remove his clothes that we were going to act out the next scene. Rest assured, I didn’t have to ask him twice! 😉
Unfortunately, I was so wound up planning for my first time anal sex experience that I totally forgot the lube, etc. Andrew sure as hell didn’t bring any so we were going to have to use our own juices if we wanted to even try. With that I started to suck on Andrews super thick cock. I hadn’t given a blowjob in quite awhile but remembered to keep his cock nice and sloppy wet while I stroked him to full erection. By now, my pussy was starting to get super moist and I figured we could use those juices too. I reached down to play with my aroused clit as I continued to suck and stroke Andrew’s now throbbing cock.
I believed we were ready for round one now that Andrew was able to watch anal sex movies in real-time thanks to that little Roku box. I left Andrew’s cock dripping with spit and then got into doggy style position so that we could both watch anal sex on the TV while attempting it in person! Everything we did seem to work on the porno scene we just watched. Surely, that would be enough. Wrong! Well, let me tell you something. . . spit might be enough for a porn star that has already had her ass stretched to the moon and back by a rock hard cock but, it sure wasn’t enough for my virgin asshole. I can still vividly recall the sharp pain as Andrew tried to push his near eight inch cock inside my anal cavity. Honestly, it was his girth, not length that was posed the problem. Andrew had one fat cock!
For some reason, I just couldn’t relax my Sphincter. I screamed as Andrew tried to shove past my anal entrance with the head of his cock. I tried to no avail to accommodate his significant girth but, had to pulled away embarrassed that my evening of anal sex was going down the shitter. . . No pun intended! I was so ashamed that I decided to go immediately ass to mouth so that I could relieve my new lover (and partner in anal crime) of his pent up sperm. I could tell he was on the verge of blue balls and needed a release. If nothing else, it showed that I was a try-sexual trooper as I got my first taste of my own ass on Andrew’s needy cock. I still regretted not being able to take Andrews cock into my ass and was going to do my best to salvage the moment with a mind-blowing blowjob!
Luckily in all those years of marriage frustration, I had not forgotten how to give head. I sucked Andrew like a high school cheerleader on prom night and worked on his cock with precision. I even forced him onto his back and proceeded to titty fuck him for good measure. It wasn’t long before Andrew shot a hot load of cum into my eager mouth. The thought of having the head of his cock in my ass only a few moments before still ran though my mind, especially how much it hurt! I didn’t want to lose focus on ending Andrew’s blowjob properly as I let his cum ooze out of my mouth back onto his near monster cock positioned nicely between my tits. I stared at the cum rope that stretched between my lips and Andrew’s now pleasured cock. I then looked up at him and winked saying, “The Best Is Yet to Cum Baby!”
As Andrew and I wound down from our Failed Anal Attempt, it was clear that we wanted to Watch Anal Sex on a regular basis in order to better understand how to take care of me and my now half-virgin ass. The pain was unbearable but, I’m convinced that by trying the proper sex toys, lube and watching anal sex movies, we will soon master my ass! Please bookmark our page and stay tuned as I keep all our valued readers of Top Rated Anal up to date with my future “Anal Adventures!”