First time anal [MF] (long) | 2016

Suzy and I dated for several years. But I don’t really understand why. The relationship was a mess. She was fun, loved life and travel, loved trying new foods, really, on paper the kind of girl I’d go for.

From a distance you’d think she was the nicest girl you’ve ever met, because that’s the side she let others see. But she was also a narcissistic, hot headed, lunatic control freak. I was really only semi attracted to her: blond hair, A-cups, small ass, amazing muscular legs, girl-next-door-lower-end-of-pretty-face, her legs are what she had going for her physically. Sex was mediocre, bordering on inexperienced. She didn’t know what to do with her body and just sort of moved around in bed like a sack of concrete. BUT, it was adventurous sex. Which may be why I put up with her controlling rage and narcissism. If I ever wanted sex, all I had to do was initiate in some way, it didn’t matter where it was. She was down for it. Like in her parents driveway (that happened) or a hotel balcony (happened too) the middle of the back yard (yup) standing in front of the window at night with the lights on in our downtown condo overlooking one of the heavy foot traffic street in our town (no joke).

Suzy loved to be dominated. Maybe there was something to that as well, like if I fucked her hard enough I might fuck the lunatic right out of her. She also loved when you played with both of her holes simultaneously. Which leads me to:

It was a Friday night and we were meeting friends at the bar next door to our building downtown. I had just finished getting ready, Suzy had just gotten out of the shower 5 or so minutes ago and was texting a friend while laying on her stomach on a towel on the bed letting her skin breathe, like she often enjoyed doing.

Standing behind her I had an amazing view of her small ass and pussy lips, which left me a little excited. I like to let sexual tension build so I wasn’t quite ready to have sex, but I wanted SOMETHING. I reached out and smacked Her ass and got a favorable but short “mmm” in response. This was my favorite sex position with her. Her ass wasn’t big enough to block full, deep entry so I could pound her g spot from behind and make her cum 9/10. But, like I said, I wasn’t ready for sex.

I bent down and kissed Suzy’s ass close to, but not in her crack. Another, longer, favorable response. So I moved closer and kissed her ass right at the curve of her crack. Another moan. Kissed the other side and licked her ass cheek a little which seemed to excite her because she opened her legs a bit.

Now, I love eating ass, it gets me rock hard nearly instantaneously, I’ve licked nearly every past girlfriends ass, but for some reason in the 3 years, at this point, with Suzy, I’ve never rimmed her ass. I’ve not even seen it actually. I’ve had multiple fingers in it, but no visual or tongue contact. So I decide to go for it given the response I’m getting.

I sort of nuzzle my face in to her ass and give her cheek a lick and kiss just shy of her hole. Now she’s moved past humming and I’m getting an audible “OHH” - I spread her ass apart and reveal the cutest little pink button of a hole I’ve ever seen and start licking around it and spiraling in to the center. This drives her crazy and she reaches down and starts rubbing her clit. I keep at this for a few minutes as I see her getting pretty worked up, but I stop abruptly, smack her on the ass and tell her to finish getting ready so we can walk downstairs. The look on her face says I’ve just left her with the female equivalent of blue balls. I’m not done with her, but I’m done for now.

She puts on her knee length blue dress and We walk down to the bar. We have drinks with our friends and have a good Friday night. About halfway through the night I lean over to her standing at the bar, I discreetly reach my hand up her skirt and slide a finger in her pussy and place a finger on her asshole and whisper in her ear as she gasps, “I’m going to fuck your tight ass tonight” and pull my fingers out and return to normal. Her look was one of surprise but not one of denial. I could see a flicker of excitement in her eye. We’d talked about how much she loved ass play and the idea of exploring anal but hadn’t actually done it yet. I’d never done it with anyone actually. (I’d tried with an ex but she had a small frame and her ass was so tight we couldn’t get it in without a lot of pain for her so we gave up on the idea) My blood is starting to flow at this point but we’ve still have a few hours to go.

We wrap up the night and saying goodnight to our friends outside the bar. We walk across the street to our building to go home, fairly buzzed. The way our building was set up, it faced the busy downtown street but the entrance was on the back; you had to walk through the parking lot on the side if the building to an alley behind it. There was a small alcove next to the keypad to the door that was semi- hidden if you were in it.

As we approached the door I’m getting hard thinking about her ass, so I pull Suzy in to the alcove and start making our with her. Her hand immediately goes to my half erection and I can’t take it. I tell her to slip her panties off (remember, likes to be dominated, is down to fuck anywhere) - she quickly complies and hands them to me. I shove them in my pocket pull my rock hard cock out of my zipper, lift her leg (she’s the perfect height for this move) and roughly shove it in to her pussy, which is so wet it may as well be lined with baby oil. I fuck her hard against the alcove wall for a short time, but she’s not being quiet by any definition - she’s naturally fairly animated during sex, but the alcohol and the exhibitionism is really taking her over the top, so I pull out and tell her we need to get inside.

Up to the condo and straight to the bed, she’s naked 5 steps in the condo before I’ve even closed the door. I enter the bedroom and she’s face down like before we left. I quickly strip and nearly dive like a dick spear in to her pussy, sliding right up her body. We fuck like this for a few minutes as she’s gotten good and worked up. I stay in her pussy but lift myself up on to my knees sort of straddling her ass. I grab her hands, place then in her ass and say “show me” - she spreads her ass apart showing me her pink button which I spit on, to my surprise, she reaches a finger over and starts fingering her ass. “Do you like that?” she asks. I do. Hell. Yes. I do. I start fucking her again, but slowly as I watch her continue with a second finger.

I grab the bottle of lube next to the bed so she can slide in and out easier. I just stop and watch this magic unfolding for a minute before I can’t take it anymore. I pull her fingers out, about to position myself to try to put it in her ass when she pumps some lube and starts stroking my cock. Holding on to it she bends it down and my body follows, I’m suddenly aware she’s rubbing and pointing my head to her ass.

Slowly I start pushing my way in. There’s a little resistance but not as much as I expected from my last experience. I’m slowly pushing in and our, trying not to go too quickly. I feel her relax as I hit the halfway mark and she tells me to put it all in. With a slow, steady thrust I push all the way, deep in to her ass as she lets out one of the sexiest moans I’ve ever heard from her. As I’m slowly rocking my dick in her ass I can’t help but think what a unique, amazing sensation this was. I reach around under her, grab her tits and start going steadily faster. She’s starting a soft “yes, yes, fuck my ass baby” I’m building up to pounding harder than I thought she’d be able to take but it’s just working her up more as she’s griping her pillow and loudly screaming “yes, oh god, pound my ass. I’m gonna cum, I’m gonna cum” when I realize she wasn’t just putting in a show. I felt her ass tighten and pulse around my Dick followed quickly by a wetness on my balls as I realize she’s squirted (every orgasm, this isn’t abnormal for her) - in my head I’m thinking holy shit she just came while getting fucked in the ass, this is amazing. And she’s still cumming!

The pulsing from her orgasm is more than I can handle and I am immediately on the edge. I tell her I’m gonna cum. In between a moan and a yes she says “cum in my ass, I wanna feel your cum fill my ass” at which point I explode and fill her ass with every drop of cum that’s been building and teasing all night and lay there on top of her until my dick goes soft and pulls itself out of her ass.

Needless to say, this became a semi-regular thing for us for the remainder of our relationship.