A different kind of first anal ... | 2016

This is a story I remembered when I saw some fine GW ass-pics, which reminded me of a FWB I had about 4-5 years ago. Being some kind of a first, it also is the first post on my newly created sex-themed blog (phantasmagoreic.wordpress.com). Thank you GW for making me remember.

Hope you enjoy it. I know I did, both writing and remembering it ...

I was browsing through Reddit’s GW section when some images (this, this and this) caught my undivided attention. And it acted like kind of a “ghost of pussy ass past” and reminded me of a previous FWB I had ’bout 4 years ago. A FWB who’s name doesn’t matter but with whom I had some wild times on and around my bed …

Since ass seems to be the word of the day, I remembered the first time I got to stick my pecker up that fuckable ass of hers. We were FWBing for about 2 months and one time, after fucking like wildlings and she came all over my cock while I came all over her face, she asked me something like “what would you do to me if you were to have your way with me without limits?”. My answer was quick, with no remorse or second thoughts: I’d oil that ass up and fuck your brains out of that butthole.

A couple of days passed and I finally got to tap that ass of hers. I woke up that saturday around noon, as I usually did back then when I was working from monday to friday, and the first thing I saw on my phone’s screen was a message that sounded like “I have 2 hours off, are you home for a special visit?”. I’ve sent a short reply, telling her “I’m already up and visitable”. 20 minutes after that she was at my doorstep, wearing nothing but her house dressing gown (a small bonus for being my 1st floor neighbour). As I took her into the bedroom she gently whispered into my ear “you’ll fuck me today the way you’ve never fucked me before” …

So here we are -on the double-sized bed- in my bedroom, when she takes the dressing gown off and assumes that exact position you see in the pic above. First thing I did was to get on my knees and start to kiss and bite that truly tappable ass of hers while she started to slowly pinch her nipples. She liked pinching her nipples, be that from her fucker or from herself, it didn’t matter. After a while she pushed me backwards and started to play with her asshole. At first around it, gently massaging around it and spreading just a few drops of massage oil. As I layed there, on the ground and watching up to her wonderful self-play, I kinda’ started to drool and got the idea of making it a private show. So I sat on the armchair and I told her “play right in front of me, I wanna watch you prepare yourself for things to cum … literally”. And so she continued her play, teasing that small to-be-fucked hole and self-slapping them ass-cheeks. I’m kinda’ pervert and voyeur in attitude, I admit, I like to watch the girls before I get to put my hands on them. So I’ve lit one cigar up and enjoyed the beautiful show in front of me. You know, that double standard attitude we men (and not only us, truth be told) like to profess sometimes, when we have that “fuck it, I’m not interested in her” look but all that’s going around in our minds is “oh, how I’d like to throw a serious fuck into her” …

Gently she started to get her thin fingers soaked in oil and, finger by finger and centimeter by centimeter, started to open her asshole. The tip of a finger at first, which slided in kinda’ hard in the beginning. Then she showed me how she played at home, when nobody’s around and she’s hungry. Two fingers started to enter her butthole, moving in and out, in and out. She started moaning and dripping from her already wet pussy, mixing oil and bodily lubricants together. All of a sudden she stopped and spread open her asshole, showing me what I was about to get from her. She spread her asshole and asked me “do you like what I’ve done to myself?”. How can one say “no” to this kind of view and attitude, I ask you?

She showed me three fingers and begun to lick them. She got them all wet and stuck them together, beginning to finger herself right in front of me. I got closer for a better view. But then again, why not for a better touch? I’ve started to rub her downstair lips and got my fingers all wet from her pussy. She grabbed me by my hand, said “I want you in me” and made me slip two fingers into her warm hole. And she was warm and tight as fuck, I tell you. Not a long time after this, she told me I had to change holes because she had a final thing to do before we can do it like wildlings. I soon found out that thing was getting me up and ready for the job-at-hand. Or rather job-at-cock. As if I wasn’t already ready …

She got on her knees in front of me and firstly begun licking the tip and shaft. She had a truly dirty look in her eyes while doing it, with a smile reminding me of an innocent teen-girl but also of a cumslut anticipating what’s to cum. Or rather come, my bad. I liked the way she did it in handsfree mode, her hands resting on my legs and her look never leaving mine. With no warning, she swallowed it all in one go and touched my balls with her lowly lip. Fuuuuuuck me, you’ve never had a DT if you’ve never felt your cock swallowed in-full and her playing with her lip on your balls! Not to get too carried away, while she gasped for air to breathe I was playing with and in her asshole using my index finger. I have a thing when doing that, I like to feel her asshole tightening up around my finger and the warmth heating up my finger. And she did exactly that, tightening her asshole and making me stuck my finger harder and deeper, ’till it all got inside her. That’s how I knew she was ready in-full for a thicker finger of a different nature …

So I took my cock out of her mouth, all drooled upon and dripping, and changed seats. She got herself on the armchair, with her backside facing me and her hands spreading open what I was about to finally conquer. She asked me to do it gently and I listened … at first. I shoved my cock up her ass slowly, tip first and centimeter by centimeter, ’till it got all inside her and she moaned like she never had one before in there. And she didn’t. She tried it a few times but had nothing but badluck on the account of the guys with whom she tried being pricks and roughing her up. Bering that in mind, I started to slowly massage her back and asscheeks and moving forth and back as slowly as I could. And as I kept at it, I felt her hand playing with my balls and her pussy at the same time, massaging and rubbing them …

I like the view from the backside, with her hair pulled to the side and my inside her. It’s an outstanding POV for me and makes me feel in control. Thing is, as I continued to move back and forth inside her asshole, she got more and more resistent to the pain and started to feel the pleasure and slightly tremble. She pushed me out of her, turned her head towards me, gazed at me and asked me (with a slight shame and timidity in her voice) “would you let me taste myself from your cock?”. I couldn’t say no, because the exact same thing was on my mind too. So I put her on the bed, spread her legs wide open, got myself sitting over her chest and let her taste herself off my cock. She found it as suckable and swallowable as ever, therefore she did it again. Magical thing it be, to see your cock vanishing in a woman’s mouth.

After she got full of … taste, I got down from her chest and found my way into her again. Let me rephrase that: found my way into her asshole again. This time with a bonus view, as I could see her pussy too. And as I could see my throbbing cock making her pussy move while I pumped my way in and out of her butthole. She’s a hard one to please, this one. Ever hungry of being fucked, she begun fucking her pussy with two fingers and pinching her nipple. I whispered in her ear “you have no idea what a view I have of you getting assfucked” and she replied with “can you show me?”. So I grabbed by the neck and pulled her closer, getting her body curved faceward and letting her see a little bit of what I saw. And it gave me a plus in matter of feeling in control, because I felt she liked the new position and was in a slight painful posture at the same time. And I liked it.

As we were engaged like that, with me sliding in and out of her and close up and personal, she started to moan and whisper in my ear. “fuck me harder, get inside me and fuck me faster”, she said. I couldn’t but listen and obey, because I’ve wanted to assfuck her since the day I’ve met her. So I started to move faster and harder, hitting her pelvis with mine every time I thrusted myself deep inside her asshole. And she kept begging for more, for harder, for faster. And I begun pinching and pulling her nipples, slapping her breasts and pulling her head backwards. She started pulling me inside her by my butt and tremble with guilty pain, her face skin getting a redish hue and her eyes moving randomly in all directions. I knew she was about to cum and I kept slapping her titties, getting them red and hurling myself into her ass.

I don’t know for how long we were at it but I do know that the pressure of her tight asshole around my cock, the look in her eyes, the moaning and sounds of pleasure as well as the sight of her getting properly assfucked for the first time all made me close to errupting. Of course she felt it too, because my cock got ready for releasing the pressure and the meant it got thicker and harder than it was. Thicker she felt it, and started mixing pain with pleasure all the while I kept pumping my way into her, harder she felt it, as I raised the tripping speed and felt like a fucking machine spiraling out of control. So she pulled by my neck, stuffed her mouth with my ear and hissed “I’m your little anal slut now, treat me proper and as you wish”.

I had to treat her my way and treat her proper. So I grabbed her legs, pulled them tight together and let myself into her completely. And by completely I mean I blasted my cum into her asshole and felt it swallow it all like a hungry mouth. She was a little surprised by the intensity of the sensation, and I must admit that so was I. I filled her asshole with my cum and tightly grabbed and hugged her while doing it and she gently bit me by the neck and ear in the mean time. She then whispered into my ear “I told you to treat me like the anal slut I am”, so I got myself out of her gaping asshole and spread her open with my hands. I turned her around, with her face beneath my groin and shoved my cock straight up her mouth. I grabbed her by the back of the neck and pulled her head up so she swallowed it all and her eyes got wide open. As if asking me “is this the way to take it all?”.

After she sucked clean all that was left inside my still hardened cock, she swallowed it all and started to pinch her nipple and gently touch and rub her asshole. And, with a serene smile and slutty look, she asked me “why haven’t you tried to convince me to do this earlier? If I’d known how it feels I would have let you convince me way earlier” …