[M]y [F]irst time doing anal

Her and I met in Spanish class during my final year of college. She was a crude, petite, dark Latina with a great ass, but her Spanish was as good as mine (not great at all). So we decided to be study buddies.

One evening she asks if if I’d like to hang out. Now my living situation at that time forbid me from having ladies come over, but being that bold individual that I could be at times, decided to risk it. I informed the girl we could only whisper if she was to be over, so she offered to not talk at all. I thought that was funny because I wasn’t really expecting any action, but did hope for some. As soon as we made it into my room, she told me to lay down on my bed. She proceeded to kiss me, then unzipped my jeans. She pulled out my half-chubbed cock out and proceeded to suck it. Deep strokes, head moving up and down, inhaling my cock, she did it all. She polished the head until there wasn’t a drop of cum left in me. After she finished me off, she told me she had to go. I snuck her out as quickly and quietly as I snuck her in.

About three days later, she texts me: “what are you up to?”

Bored and not wanting to do any homework, I replied, “nothing. Just avoiding homework. You?”

“Nothing. I kinda wanna get fucked tonight and seeing if you’re up for it.”

“I think I might be up for helping you out with that.” I thought I was so cool trying to play it down.

I picked her up from her apartment about 20 minutes later. We both really had nowhere to take this since she shared her room with two others and I had my restrictions, so we drove into an alleyway not far from her apartment.

We get into the backseat of my car, stripping down, kissing one another. I suck along her little tits, biting her neck and pulling her pants and panties off. As soon as the condom is on, I waste no time trying to guide my cock inside her pussy. Her being so small, she was ridiculously tight. My cock pressed on, trying to fit every inch inside of her tight, shaved little pussy. She screamed, gasped in my ear. My thrusts were slow. I can feel so much of her as her thick, short thighs wrapped around me. Her nails dig into my back and comb through my hair.

“Do you wanna fuck my ass?” She moans into my ear.

I’m caught off guard by the question. Especially since I’ve never done it before. “Uhhh… Yeah…”

I pull out of her. Her pussy drips onto my backseat. The tip of my cock begins teasing her asshole. I struggle trying to slip it in.

“Take the condom off,” she tells me.

I take it off. My cock is pretty lubed up from the condom, but her ass is so tight, tighter that her little pussy, I have to press slowly inside her. Her legs high in the air, feet pressing against the ceiling of my car. She gasps as I keep pressing my cock into her. Once I fit every inch of me, I slowly begin sliding it out, leaving just the tip still in her. Then fully back inside her. Back and forth, over and over. Getting faster as I loosen her ass up more. It’s still so tight it brings the urge to cum more and more.

I’m thinking “I gotta change positions or pull out because I’m going to bust my load in this girl.” Before I could even pull out, shift her leg, or change position, my load unloaded deep in her ass. My hands squeezed her cheeks hard, my hips pressed hard against her.

“Did you just cum in my ass?”

“Uhhhh…”

She knew. Wasn’t surprised, but knew. “You’re lucky it’s just my ass. Besides, I think I got some Plan B back at my place just in case.” My cum poured out of her tiny little ass after my cock and onto the floor of my car. Luckily I had a few napkins right next to us.
What a little mess we made.

Source: reddit.com/r/gonewildstories/comments/iyr3el/my_first_time_doing_anal

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