The One Where I Did Anal for the First Time [MF]

Admittedly, I’m an ass man. When I check out women, my first glance is almost always at their butts. Pretty much every woman I’ve ever been with has had a nice butt. Despite my dedication to the derrière, I’ve not had that much interest in anal.

This story takes place after my very first serious girlfriend and I broke up. We were the ones who lost our virginities together. We were going to get married. We were also young and dumb, but I digress. We’d talked about anal before. She was interested for a time. When we had sex, I would eat her ass. She said she really enjoyed it. Being young and inexperienced, though, I rushed into anal too fast. I wasn’t jamming my dick in her or anything, no. But I did stick my pinky in her ass one day, with no lube, and almost no build up. She yelled at me (rightfully so) and that was the end of sexy times for the day, and the end to our talks about anal.

We broke up several months later. It was mutual. One of my first weekends as a single man lead me to a house party at one of my friend’s house. When a majority of the guests left, the six of us that remained went in the back yard and sat around a fire, playing truth or dare on someone’s phone. The game got pretty heated. Two of the girls there kissed. I kissed one of the guys (coincidentally, I also learned I was not into guys that night). I got to feel up the girl with the biggest boobs. Secrets were spilled. Horny teenagers were horny. I ended up getting one of the girls (her name was Amber) numbers that night before I left.

Amber was a tall girl, about 5’10’’. She had long legs, with thick thighs that lead to a very nice, plump ass. Her waist was slim, because she was super self conscious about her weight and watched it with the utmost care. She had c-cup breasts that she liked to keep hidden under baggy shirts. Her auburn hair was shoulder length. She had a round but cute face. She looked kind of mousy. She was a good looking girl, but she thought she looked like a potato (her words).

When I got home, I planned on going to sleep, but she texted me pretty much as soon as I got in my door. The conversation was light and friendly until we got on the topic of the game. Things took a turn for the sexual. We talked about what we liked, things we wanted to try. She said she loved having sex – all kinds of sex. I asked her about anal. She said she preferred it since she wasn’t on birth control and she didn’t have to worry about getting pregnant. Our dirty conversation went from our likes and dislikes to what we would do to each other if we were with the other one right then. When our fantasy ended, she told me she was going to bed, but that we would have to make it a reality soon.

It turns out, I didn’t have to wait long. The next day she texted me telling me she had her house all to herself until late that night. We made plans and she picked me up at my house. When I got into her car, I noticed she was wearing a white cami and athletic shorts that left little to the imagination. When we got to her place, Amber and I watched tv, I showed off my sick Rock Band guitar skills, and we talked and had a good time in her basement. It wasn’t long, though, before we made our way to her bed room. We had many hours until I needed to be home, and even more until her family would be back, so I decided to take it slow and build up the tension.
Amber pulled out her phone and opened the truth or dare app soon after we sat on her bed. My memory escapes me of what we were dared to do and what truths were told. All I remember is that I was dared to tickle her. I did. She fought and kicked and rolled around until she somehow managed to get on top of me. Her hair cascaded onto my face. She held her lips just centimeters away from mine. It was going to happen.

I kissed her.

She kissed me back. My hands went from on her hips to on her ass. I have large hands, and even they weren’t enough to fully grasp this ass. I gave her ass a smack and she moaned and giggled while we made out. I took off her shirt, revealing a pink and white polka dot bra. I grabbed her neck and kissed it, sucking it lightly as she dry humped me. My hands traveled from her ass up to her boobs. I squeezed them a little, then I pushed her off of me.

I kissed her lips again, then went down to her breasts. I put my face in between them and she shook them in my face, laughing at how much I was enjoying it. My fingers traced the outline of her shorts, feeling the soft fabric of her thong that was starting to rise out of it. I pulled both of them down to reveal a gorgeous innie pussy. I went to town on her. I put my mouth on her clit and sucked in. She loved it. I hit her clit with the tip of my tongue, flicking it back and forth a few times, then I used the whole length of my tongue to lick from her hole to her clit, back and forth, again and again. I put a finger in her moved it in and out, but she gave the me “come hither” motion. I started doing it and she was coming in no time, pulling my hair and clawing at her sheets.

After she came, she said it was my turn. I took my shirt off and she slid my shorts off. I laid on her bed and she went down on me. I knew she was experienced from some what she had told me before, but I had never experienced anything like this before, having been with only one other girl. Her tongue swirled around the head of my dick before she swallowed the whole thing. It hit the back of her throat and she didn’t gag. Her head bobbed up and down furiously. She took a hand and gripped my shaft. She stroked me up and down and she her mouth worked the head again. I was going to come soon if she kept doing this, so I grabbed her head and pulled her up to me. I kissed her while she was still stroking my cock.

“Let me fuck you,” I said.

“Do you have a condom?”

Of course I didn’t. I had prepared myself that day, but somehow completely forgot about it.

“Fuck. No.”

“That’s okay, you can fuck my ass. I don’t mind.”

Holy shit. I was probably stammering my agreement because she was laughing again. I told her to bend over the bed. She did as I told her and I got behind her and spread one of her cheeks so I could see her asshole. I lined up my cock and was ready to put it in when she asked what the fuck I thought I was doing.

“I’m gonna put my cock in you,” I said, thinking we were dirty talking.

“No you idiot. You can’t just do that. Warm me up first. Eat me out. Then we’ll lube you up.”

I dropped to my knees and spread her asscheeks in front of me. I wasted no time and plunged my face into her ass. I rimmed her and kissed her asshole. She told me to get lube from her night stand and put it on my finger. I lubed up my finger and gently put it in her. She moaned as I moved in and out. At times I would start to go too fast and she would tell me to slow down. When she felt she was ready, she had me lube up another finger. I fingered her asshole for a long time while she rested her head on the bed. I hadn’t noticed it before but she was looking back at me while I finger fucked her. The look in her eyes was that of pure lust. She was fucking loving this.

She finally said she was ready for my cock. I lubed myself up a lot, to the point I could barely grip it. I put a few drops of lube on her asshole for good measure and lined myself up again. There was some resistance as I pushed in, but I managed to get the head in. She moaned and arched her back. I went in very slowly and pulled out even slower. She reached back and grabbed my hand. My pace picked up a bit. She let out a squeak so I slowed down. Then she said something to me that almost put me over the edge.

“No. Keep going. I like the pain.”

I pushed into her. She yelled. I decided that was too hard, so I slowed down again and eventually found a rhythm that felt good for both of us. She said she wanted to lay on her back, so I pulled out and she flipped over. I re-entered her ass with a little more ease this time and started going again. At first I watched her tits bounce in her bra and wondered why I hadn’t taken them out. Then I looked at her face. Amber was staring at me. When our eyes locked, it was like she was staring into my soul. This only made me pick up the pace. She grabbed my face and pulled me in for another kiss. I grabbed her tits and pulled down her bra. I pinched one of her nipples. I pulled away from our kiss and put my hand on her neck. I squeezed lightly on her neck and her hand went from my face to her clit. She started rubbing herself as I thrust in and out of her. Soon she was having another orgasm. The clenching of her body was too much for me and it sent me over the edge. I plunged deep into her ass and shot ropes of come into her. I grabbed her face again and started kissing her, my dick still in her ass.

I pulled out and we continued to make out until it was time for me to go home. Unfortunately this was the only time I ever hooked up with Amber, though it wasn’t for lack of trying. At the end of the day, she was the type of girl who fucked someone once and moved on. I can’t fault her for that. More power to her. I definitely wish I could have seen her again though.

Source: reddit.com/r/gonewildstories/comments/8pyxmu/the_one_where_i_did_anal_for_the_first_time_mf