The Time I Hate-Fucked a Right-Wing Conservative in Honor of Obama’s Inauguration [MF] [Craigslist]

I have a real distaste for sentimentality, as it strikes me as backwardly myopic and is a slippery slope to conservatism, but thinking about the casual encounters section gives me the sentimental feels, and segues perfectly into one of my favorite CL stories I have. Craigslist democratized casual sex way before Tinder came along. And to be honest, if Tinder existed when I was in my heyday of promiscuous activity, then I probably would not have even bothered with craigslist. While the casual encounters were there for the taking, it really was a whole lot of work, and required wading through the cesspool of human desires, which was interesting to me on a number of levels, but also kinda sad. The saddest part was not in the gaze itself, but in seeing my reflection in the pool. There are times I lament the demise of CL casual encounters as a reflection of some puritanical social reaction to what has become a society much more open to casual sexual activity, specifically women being more casual and open with their sexuality. But I know that’s pretty black-and-white, and think the extinction of CL casual encounters is just part of our internet aided, virtual evolution.

This story took place in 2010 or so, sometime after Barack Obama won the office of the Presidency for the first time. I was a 32 year old man who was living in Los Angeles when I posted an ad in the M4W section of casual encounters. The ad was a celebration? …more like a full on gloat-fest, where I basically said I wanted to celebrate Obama’s election by hate fucking some horse-faced, Ann Coulter looking conservative woman. I cannot remember all of the details, but it was mostly a joke post. With that said, I knew that my writing was something that was very well received by some women. The ability to titillate and interest another person with words is a mind-fuck that, more often than not, leads to a very good physical connection as well. So in a way, the post was not just a joke, but a virtual line hooked with bait which I set and forgot about.

I moved from LA around that time, to a city a little further north up the coast to move in with my new girlfriend, but would routinely renew the post because I thought it was funny. I got a response a number of months later. It was not the first response from the post, but it was the first one seriously responding to the proposition, rather than just saying that my post was funny and awesome or whatever. I’m a little hesitant to provide too many details about this woman, but for the purposes of this story we will call her Ann Coulter. I think most people know how this dance gets started when dealing with anonymity and initial electronic communications before a casual encounter. You try to get a feel for if this person is a troll, or if they are who they say they are, or try to get a sense of their motivation, and also find out what they look like, because I was not in a place in my life where I would just stick my dick in anything. I was working out daily, and in really great physical shape: thin and chiseled, with wide shoulders, thin waist, tanned skin, muscular legs from playing soccer through college, brown curly hair and blue eyes, and was like a kid in a candy store living in SoCal surrounded by beautiful women. I also had a gf, who I was being faithful to at that point (she ended up cheating on me also), but this was something I could not pass up.

Our emails back and forth were filled with a mix of vile and interest and humor. She was 55 and in a sexless, loveless marriage with a successful and wealthy man. She was born into wealth and acted like it. She rolled out the socialist/communist tropes typical of sheltered bourgeoisie who think their excess is enough to assuage the masses as their shit rolls downhill. She was a success in her own right, and was cultured as well. Knew good art and literature and had some cultural sensitivities that would peek through. The kind of girl who got a liberal arts degree because she knew it would piss off daddy, but he still paid for her studio in France so she could pretend she was a painter for a year, before she moved back to the states, married well, popped out a kid, and started her own business when she was settled. At that point in my life I still felt passionately about trying to take action to ensure my values were represented in our socio/political sphere. I no longer give a shit, but I did then (as an example of my ambivalence, I could no longer hate fuck a Trump supporter – I would go a big soft one at the thought).

We are emailing back and forth, things are getting a little steamier and building toward what could be a pretty awesome climax. She is living in Beverly Hills or some shit, and I am not a long drive up the coast. She sends me a couple of pictures of herself in provocative but flattering poses. I’m thinking as long as she’s passable we’re gonna do this, but I am skeptical as a CL pro. She is telling me she wants to be choked and face fucked and ass fucked, and has never done anything like that before. I showed her the growth of the proletariat and explained how it would topple her classless asshole, and dump my surplus value down her throat. We eventually decide she will drive to the city I live, get a hotel room, and I will come during my lunch hour to fuck her senseless.

I arrive at the hotel and Ann Coulter meets me outside. She says she wanted to make sure I’m not a serial killer before we go into her room. She is not particularly horse-faced enough for my liking in this scenario, but she is a larger-framed woman, standing my height at 6-1 (said she was a former model) and was curvaceous. She had big beautiful natural breasts that hung just right, and wide child bearing hips with impossibly soft skin from years of bathing in the blood of immigrant sex-slaves. She had an acerbic face, from years of looking down on others, which also bellied her age in a rather pleasant way. In terms of a CL casual encounter, this one was a fucking win.

She was clearly nervous as we get to her room. I act nonchalant as I walk around the entire suite, opening doors and looking in the shower, making sure I’m not about to be a victim. As I am doing this she is just kinda hanging out in the sink area outside of the bathroom, where there is a large mirror. I cannot remember how she was dressed, but I’m sure it was the uniform of the outwardly innocuous, middle-aged capitalist. As soon as I felt comfortable in the safety of my kidneys, I approached her and softly kissed her on the lips for the first and only time, and pushed her to her knees and fed her my cock, exactly like Sarah Palin would’ve wanted me to. I pinned her head against the wall while I forced my half flaccid dick into her throat. She gargled and spit, with her head knocking against the wall, while I worked up to full mast inside of her throat. I was watching myself fuck her face in the mirror, occasionally looking down at her sad, tear-filled eyes, wondering if it was my cock that was making her cry, or the thought of 8 years of an Obama White House on the horizon. She asked for a break to breathe on occasion, which I was happy to oblige, despite her support for waterboarding.

Her face was getting sloppy, so it was time to move to the bedroom. Her clothes came off, and her alabaster skin gleamed. She did have the softest skin. She was well taken care of. Her pussy was hairless and smooth as a baby’s bottom. There’s no such thing as missionary in the game of hate fucking. On to her knees she went on the bed — her big, white, barely-touched conservative ass in the air ready for a pounding. I wish I could say I went in dry, but her pussy was as wet as her glazed face by this point. I stood above her on the bed and started pounding away, a dollop of spit dropped onto her asshole before two fingers follow, DP-ing her with my cock and fingers while she moans into the comforter. I would be lying if I said I remembered the shit I was saying to her as I tried to fuck her through the bed, but I’m pretty sure it was funny as hell. It was probably hot at the time, but funny as hell in retrospect, much like all the Marxist shit I’ve been saying so far in this story. It was all just stream of conscious vitriol and celebratory gloating….with a side of dick.

We switched positions a couple of times, but always with doggy style. She wanted me to fuck her ass, but I was using a condom, and ass-fucking with a condom is really no fun for me. I was more interested in fucking her face. The grand finale I moved her to the edge of the bed, with her head dangling off the side, and fucked her face with my condom flavored dick until I shot a load down her throat.

We both caught our breath, and I was about to put my clothes back on to leave when she said, “Wait, I just want to look at you for a little bit.”

Playing to my ego worked wonders at the time, so I chuckled and obliged while we talked during the come-down.

I never really knew if she truly was a right-wing conservative, or just a lonely woman playing a role to fill the void of loneliness in her life. Looking back on the experience now, and typing it all out, I see how my being the object of her gaze quickly switched the roles back to the servile and the served, with all of my excess energy and anger doing nothing but adding the coffers of her pleasure. There’s a bit of poetic justice in that…because shit is just the same as it ever was.

Source: reddit.com/r/gonewildstories/comments/95rk00/the_time_i_hatefucked_a_rightwing_conservative_in