Anal: First Experience [MF]

Not long after my then girlfriend (21 at the time, now wife) and I (24) started dating is when I started to push the boundaries of her sexual experience. One fond memory I have is the first time I knew I would have someone who would be able to keep up with my sexual desires and (after getting to know each other more) someone that would want to push her own boundaries.

We had just gotten back from a night out getting dinner and drinks when we made our way to the bedroom for some raw new relationship fucking. As she went to the bathroom, I began to undress. Knowing full well what I was about to get, my cock was already hard at the thought of my gf sliding her wet pussy down my 7 inches. I laid down on the bed with my shaft sticking straight up in the air. I resisted the urge to jack off or touch myself because I wanted her touch so bad.

As she walked out of the bathroom, she had obviously found my dress shirt from the night before, still with the scent of my cologne. She walks over with her perfect C cup cleavage on display through the top few buttons and her perfectly shaved pussy peaking out from the bottom of the shirt as her legs moved.

As she climbed on top, her pussy was already dripping in anticipation of me being inside of her. Now, she has always loved my dick and I have always loved her pussy. Its one of those things where they feel like they were made for each-other and fit perfectly when I lightly press the tip up against her cervix.

Seeing her in my dress shirt climbing on top of her dick to do as she pleases just about sent me over the edge. Although neither of us are really into creampies (at least vaginal), I was ready to pump as much cum as I could into her.

She slowly eased herself down onto my dick making sure her wetness covered every inch. Shes always been great with a quick ego boost, saying things like “God your dick is amazing.” And “fuck your dick is big.” You cant hate her for that lol but it definitely didnt help my approaching orgasm and her pussy grip wasn’t helping either. She continued to slide up and down, her perfect pussy lips hugging my cock and creaming all over my dick and balls.

I slightly sat up to try and prolong the pleasure and to make sure I didn’t unexpectedly explode in her tight cunt. As I sat up I licked her cleavage, hunting for each of her perfect nipples. Ive never been much of a big boob guy so I hit the fucking lottery with her. Perfectly shaped c cups with nipples just big enough to play with my tongue.

My hands then began to wonder. I might not be big into boobs, but ass and pussy are things I greatly appreciate. Her pussy was already heaven. Her boobs already had bite marks. I wanted to take it up a notch and see how comfortable she was with me. My hands felt down her ass until I was spreading her, exposing her working pussy and tight little virgin asshole.

Having had some experience with ass play, I decided to test the boundaries. As she was riding and sliding all over my dick and balls, I was becoming increasingly wet everywhere from her soaked pussy. I collected some of our liquids and began to lightly rub her perfectly clenched asshole. The first touch had my brain going crazy. I couldn’t decide if I wanted to continue, blow my load in her, or flip her over and eat her from behind.

As I began to rub her asshole more I was gauging her reaction, not knowing if she has had any experience with ass play before. I obviously didn’t want to just go full tilt and start fingering her ass just because it felt good, but I didn’t want to stop it either. As she picked up her pace I asked her if she was okay. “Mhmm…” she moaned as she kissed me and continued to slide up and down her favorite dick.

I got brave. With more of our fluids on my finger I spread more all over her asshole and began to push in. I was paying close attention to her the whole time. Sex is fun, pain can be fun, but unwanted pain during sex is a no go. My index finger continued to push into her surprisingly relaxed asshole. First knuckle was in. She continued to ride and moan. Pushing a little more I got to my second knuckle. To my surprise she continued to ride like her life depended on it.

Almost knowing I could do more to her I wanted to be sure, asking “Have you done anal before? Do you want to get fucked in the ass?” My shock might’ve overtaken me as she replied “No one has ever tried anything back there.” At this point I started to fuck her harder with my finger still buried in her ass. She was getting closer and closer to cumming and I wanted her first double penetration orgasm to be perfect.

As we fucked I knew she was getting to the point of no return. At that moment I pushed my dick as far in her as I could while continuing to apply pressure to her ass, but not pushing in more. As she convulsed beginning to cum I kissed her telling her “that’s my good girl.”

I could feel each contraction tightening around my finger in her ass and her squeezing my cock with every single one of her muscles. I could also feel my cock with my finger, which was an insanely intimate experience knowing that a few weeks prior we didn’t even know each other.

As her orgasm subsided, it was my turn. I removed my cock from her tight grip and removed my finger from her ass. I flipped her on her back and started to pump her still soaked pussy knowing I just gave this woman her first DP orgasm. Needless to say I didn’t last long as I pumped into her hard, my cum was about to fill her tight pussy. As I reached my climax I pulled out and without skipping a beat she grabbed my dick and jacked me off onto her perfect chest. Her favorite thing is my cum on her skin. Anywhere on her skin. And I like to think this is the moment where that need started.

After we came down from our orgasms, we were able to talk more. I wanted to know more about why she was so comfortable with me playing with her ass. She admitted she had been interested but her past partners were not into it (“scared” was the term I think she used to describe them lol) and when I started to touch her she wasn’t going to stop me.

This simple act would lead to an anal addiction and many many more fun experiences. Her craving my dick in her ass, buttplugs of all shapes and sizes in public and private (beach, pool, weddings), anal creampies, really anything to do with her ass.

Source: reddit.com/r/gonewildstories/comments/12nn0b3/anal_first_experience_mf