My first year as a single man in a very long time [MF][Ex-GF][Anal][Part 2]: Taking my ex-gf’s anal virginity

Part II: Taking my ex-gf’s anal virginity

**Background**

Before I get into this story, let me first explain why this was especially amazing: our (my ex and I) sex life was very tame. We fucked pretty regularly, she was down for the occasional blowjob, but really nothing eye opening (i.e. never did anal or threesomes).

**Intro**

Alright so a few days after we broke up, we start texting each other again. I know, I know, I know: don’t fuck your recent ex-girlfriend. I think I’ve heard this from every male relative over 30 since I was probably 14. “Don’t do it, (INSERT STORY ABOUT WHY THEY REGRET DOING IT)” But my ex-gf is still smoking hot and something very strange happened once we broke up: we gave zero fucks about what the other person thought. This quickly resulted in both of us disclosing all the sexual fantasies we’ve always wanted to try but too afraid to bring up. To my utter shock, I soon discovered she’s down for some pornstar level shit (e.g. anal, threesomes, rimjob, etc.). Call me cautious, but part of me is still hearing the words of my male relatives in the voice of Admiral Ackbar from Star Wars: “IT’S A TRAP!”

But I’m horny and just way too fucking curious to turn down this opportunity, so I suggest we get together for one night of crazy break up sex. She acts hesitant and doesn’t respond to my text the rest of the night. The next morning, she accepts my offer and we decide to meet up that night; no dinner, no cuddling, just fucking. I grab condoms, condoms, and more condoms (she’s “allergic” to the pill). Around 4pm that afternoon, she sends me a text: “make sure you bring lots of lube, my asshole is tightttttt.” Guys, this girl has suddenly transformed into your stereotypical Southern belle: a lady in the street, but a freak in the bed. We had never even engaged in ass play, so this was fucking music to my ears! I leave work immediately, stop at CVS to grab some lube, and head home to get ready for the night of my life.

Around 7pm my ex-gf’s car pulls up outside my apartment. My dick is hard as a rock and while I suspect I’m in for the night of my life, I have no real idea what I’m about to experience.

**The Good Stuff**

My ex: 5’3, maybe 120lbs, long blonde hair with slight curls, light tan, perfectly formed C cups, average ass, below average face, and you’d assume she was the “waiting until marriage” type if you saw her. I can’t really identify the characteristic that gives off this impression, but all of my friends agree. She just looks like an innocent girl, but she’s not, at least not anymore…

She enters my apartment and I can tell immediately it’s going down. She throws her purse across the room, grabs my hands and puts them on her tits. I barely have time to notice how sexy she looks in her tight blue dress when she says “remember these?” I nod hesitantly. She moves my hands to her ass and says “remember this?” I nod again, my boner painfully pushing against my jeans. She then takes my right hand and puts it underneath her dress (no underwear) and onto her pussy and says “remember this?” I’m about to die and I quickly nod. “For tonight only, this is all yours, but let’s be clear: you’re not my boyfriend anymore, you’re a fuckboy…so use me as your fuck toy.” I pick her up and we start going at it like fucking animals. Her hands are all over my hair and we are practically panting our breathing is so heavy. I’m headed towards my bedroom but as we pass the couch she nudges my arm to let her down and says “No, I need you right now.” She bends herself over the couch in doggy position, I lift up her blue dress, and I don’t even have to check before pushing my dick into her. The warmth and wetness of her pussy is fucking heavenly. But a moment later I freeze and remember the condoms. Call me whatever you like, but I wasn’t about to get my ex-gf pregnant. I pull out, grab a condom out of my pocket, roll it on, and then go back to fucking her from behind. I can vividly remember in the moment thinking to myself: you know, if our sex life had been like this, maybe we wouldn’t have broken up. But anyway, back to the story.

Let me be clear: this isn’t “I love you” fucking; this is straight primal fucking. My hands are firmly gripping her hips as I slam my dick into her repeatedly. With each thrust, the tone of her moan decreases in pain and increases in pleasure. Her moans are filling my apartment and unlike pornstar moans that are loud and fake as hell, these are soft, real moans. “Mmmm spank me fuckboy,” she says after a moan. Keeping my left hand on her hip, I gently spank her ass with my right hand. “Harder…” she whispers. I smack her ass a little harder and she lets out a sexy moan before a slightly louder “harder.” I smack her ass harder, which is instantly accompanied by a moan of pain and pleasure. “Harder!” she says demandingly. I take my open palm and smack her ass as hard as I can, my hand stinging after impact. A loud “FUCK” escapes her breath. Keeping my dick inside her, she leans back, stares into my eyes and says very calmly “fuck me like a whore.” Her ass is practically all red at this point and you can only slam your dick so hard, so I grab her hair into my fist, pull her back, and fuck her like a whore. Each thrust is full force, my right hand wrapped tightly in a fist around her hair and my left hand holding her shoulder for balance. I have never in my life fucked a girl like this and I probably never will again. I eventually push her down from doggy into prone, place both hands on her ass, and relentlessly fuck that pussy. Her breath gets louder and her intermittent moans become one long building moan. I feel her body start convulsing around my dick and she cums hard. I pull out just to look at my dick and the condom is fucking soaked. She lays down on the couch, looking fucking exhausted and closes her eyes. I’m thinking to myself “great, back to normal.” But with her eyes closed and in a barely audible voice she asks “you want to put it in my ass?” I nearly cum as she finishes the sentence, but am able to hold on before an excited “please” escapes me. I race into my bedroom, grab some lube and nearly skip back to the couch. She’s still in her post orgasm heaven, so she just flips onto her stomach and presents her ass for fucking.

**DISCLAIMER**: You can’t just decide to have anal sex; she almost certainly had been preparing her ass all day for this (Google it before you try this). Seriously, do not just try and stick your dick in a girl’s ass, she’ll rightfully hate you and you’ll never look at your dick the same way again. I know you think they do this in porn on a whim, but those girls have also been preparing their ass all day too.

I grab the lube, pour a little bit on my fingers and push my thumb around the rim of her ass. She’s still so deep in post-orgasm heaven that she doesn’t even flinch. After a few circles, I push my thumb in and start moving it around. I then add another finger and she finally comes out of her post-orgasm state and starts wincing, her asshole clenching around my fingers. She starts to relax again and once I’m rotating my thumb and two fingers in her ass, I think she’s ready. By this point, the condom has become completely dry so I switch out and pour nearly half a bottle of lube on my dick, my fingers, and her asshole. My couch will never be the same again.

After pushing the head of my dick against her asshole for about 2 minutes it finally pops in. I slowly push in a little bit more with every other gentle stroke. Jesus that was easily the tightest asshole I’ve ever fucked. I look down and see her fingers tightly gripping the couch cushion. She might be my ex, but I still feel bad that she’s not enjoying this, so I use my non-guiding hand to rub her clit. The instant I start doing that, the tension in her fingers release and the rest of my dick slides in easily. This was another moment I can vividly remember because I would never think this girl would ever be down for anal, but here I was, balls deep in her ass. I slowly start fucking her ass as I rub her clit and gentlemen, I highly recommend this move. Having a girl into you fucking her ass is infinitely more fun than one who is reluctantly letting you fuck her ass. “God you’re such a good fuckboy” she moans, looking back at me with a dirty smile. “Such a good little slut, taking my dick in your ass,” I reply. She lets out a high pitched moan as I thrust my fingers into her pussy before returning them back to her clit. She then puts her own fingers inside her pussy and says “I’m your little fuck toy (insert my name), so fuck me like one.” I’d love to tell you I fucked her ass for 20 minutes but about 30 seconds later I’m feeling it and I tell her I’m getting close. She moans “cum in my ass baby” and as you can imagine I came right then and there. And this was just the beginning of an incredible night.

After recovering, we fucked some more, she gave me a rimjob in the shower (had never tried it before, honestly kinda meh), she sucked me off, and we passed out in my bed. When I woke up the next morning she was already gone but had sent me a text: “I shouldn’t have done all those things last night. That was wrong. I think I’m gonna need a spanking tonight for being such a bad girl ;)” My head was about to explode…this girl went from pretty tame to a complete freak.

Part III Teaser: Face fucking the boss’ daughter

Source: reddit.com/r/gonewildstories/comments/8nd9qy/my_first_year_as_a_single_man_in_a_very_long_time