Didn’t see this coming. [MF]

Anna and I have been friends for as long as I can remember. We met in school sometime around fifth or sixth grade and for some reason stayed friends to this day, both of us being 23 now.

But the thing about us is that it had never been romantic, mostly because she dated one of my best friends and my next door neighbor for almost 6 years. Anna was actually probably the best wing man I’ve ever had and has been directly responsible for some of the best sex of my life without being the one who my cock was inside. She always made visiting her at college worth it because, as it usually is, a gorgeous girl like Anna tended to have extremely good looking friends. And when these girls saw the profound affection Anna and I had for each other knowing we weren’t romantically involved, it seemed to immediately make her friends see me as someone who they could trust for casual sexual encounters.

But this story isn’t about those (awesome) encounters.

Anna lived in the city and went to the large state university pursuing a degree in nursing. Most of the time when me and Anna would hang out it was because I, who had a job and lived outside the city but went to the community college part time in the city, would come in every few Saturdays to get my tests for my online classes in.

“Hey there, what’s your plans tonight?” I messaged her after finishing my last test.

“Drinks :) you’re welcome to join me and Emma;)”

There was a reason for the winky face. Me and Emma had.. ummm.. met before. Emma was actually one of those girls who, if you got her out of that college environment and could convince her that settling down is worth it, most guys would see as girlfriend/wife material. Insanely smart and witty, confident as hell, and driven and disciplined to the extreme. And downright stunning to boot. She was a tall blonde girl who had perfected the laughing unimpressed eye roll, a look she had given me several times the night I had managed to charm the clothes off of her. But like I said, this night was not about her, even if I thought it would be.

“Sounds like a good time haha. when should I show up?”

“3:30 or 4 will be good, see ya then”

Now one of the things that made this night different from all the other times was that this time Anna was single. Her and Brady had broken up, and it was something that I had heard both sides of. The two were not bitter towards each other but it was clear that they wouldn’t be getting back together. The night in question was probably about 4 months after they had broken up and the first time I had been with Anna in her college environment since the breakup since she had spent the previous three months home for the summer.

When I arrived I was greeted with a hug. Anna was normal height for a girl, maybe 5’4” or 5’5”. She had shoulder length black hair but lighter blue/gray eyes. Her body was one of a high school athlete who managed to still work out 4 or 5 times a week. Her tits were on the smaller side, and she had a tight little booty that still stuck out because of her athletic build.

We went to her room and I laid down on her couch as she sat at her mirror and did her make up and we talked the way friends who had known each other since puberty do. About how my job was going. About how she was bordering on alcoholism but still had a 4.0 so hey who cares. Normal stuff. As we were going back and forth there was a knock and then an immediate entrance by someone who clearly didn’t know I was in there.

“Hey Annie can I borrow that really cute top you wore last weeohh.”

Emma abruptly cut herself off when she saw me because she was only wearing a bra and some booty shorts.

“Hey Emma, is that what you’re wearing tonight? That’s a great choice” I laughed followed by a snicker from Anna

Emma blushed but smiled at me.

“Hey Sam. Yeah I decided to go for the dirty whore look tonight”

“Well I have to say you’re nailing it”

Emma laughed and rolled her eyes at me, then grabbed the shirt she was looking for from Anna and left the room.

“You could at least wait till we get to the bar to start flirting with her” Anna said with a knowing smile.

“Come on. She walked in half naked. What was I supposed to do?”

And the three of us went out and had an incredible time talking and getting ourselves tipsy. About two hours in though the night took an unexpected turn.

“Cody!” I heard Emma yell as a tall handsome kid slid into her side of the booth.

Now I could have been bitter about how clearly into this guy Emma was and must have been for awhile, but honestly I couldn’t be mad. The guy was cool as fuck, confident but humble, and it didn’t take long to notice how intelligent he was.

I turned to Anna who was sitting beside me and whispered so that only she could hear.

“I guess no fun for me tonight huh?”

“I think you can handle just kicking it with me tonight” she said as she punched me in the rib.

I rolled my eyes and pretended to be annoyed.

“I guess so”

And then something happened that had never happened before. Anyone who would have walked by our table would have thought the four of us were on a double date. Emma and Cody were clearly enjoying each other’s company but so were me and Anna. Eye contact was lingering. We were grabbing each other in the thigh when we needed the others attention. Me and Anna were naturally pretty open people with good communication skills but that wasn’t the mood this time. This time we were openly flirting. I think I even caught an eyebrow raise from Emma once she eventually caught on to where Anna and I’s night was headed.

The girls’ plan that night was to leave the bar and go to an actual party somewhere so after a couple hours of palpable tension building between me and my lifelong friend at the bar, we caught an Uber back to the girls’ house.

Me and Anna got back to her room as we both needed some heavier clothing as it had gotten kind of chilly. However, at this point in the night we were both intoxicated so you can guess what happened next.

I passed out on her bed while she, in a state of drunken confusion, was having a wardrobe breakdown and “couldn’t find what she needed”.

Anna had noticed me passed out and decided to use my sleep as privacy because I awoke suddenly to the sight of Anna wearing a crew neck hoodie and a scarf but no pants on and in her underwear, as if she had only conquered half of her goal to dress herself for the party while tipsy.

I laughed at her and she jumped a little bit, realizing I had awoke.

“I think you’re forgetting something An”
I said as I laughed at her.

Anna rolled her eyes and smiled at me

“Very funny. No I can’t find the pants I want to wear. It has to be those ones.”

“Are you sure you can’t just go like that? I guarantee you’ll have all the male attention you want”

She met my gaze

“Exactly how much male attention do you think it is that I want?”

She then proceeded to hump the air like Elvis to break the tension I had just built by undressing her with my eyes and making sure she’d seen it.

I laughed and said

“It’s a little different tonight, isn’t it?”

She took a step towards me and grabbed her phone from the bedside table, looked at me and smiled and said “a little bit” and read the text message she had just received.

“Emma and Cody…. aren’t coming.” Anna giggled. “I guess they were having trouble changing clothes for a different reason”

I looked up at her and she looked down at me. Before I knew what was happening, she had bent over and placed her mouth on mine. It felt like a tentative kiss, as if she almost felt like she shouldn’t be doing what she was doing.

She stood back up and smiled at me.

“What was that for?” I asked

“Don’t be stupid Sam” she replied condescendingly, but with a smile on her face.

I wrapped my arm around her waist and pulled her on to the bed as I rolled over so I was facing her face to face in the the opposite direction of where I had been laying before. I rolled in between her legs and on top of her and kissed her deeply. She moaned softly into my mouth and met my tongue with hers.

As we were making out, she had wrapped her legs around me and I began grinding my growing erection against the area of her panties covering her pussy.

I pulled my face from hers and began to kiss her neck and bite her earlobe.

“I bet I’m not the person you thought would be in your bed tonight” I whispered in her ear.

“Or I knew Emma and Cody had planned to meet up all along and I knew exactly what I was doing” she replied in lustful defiance, as if she was extremely proud of the fact that she had seduced the fuck out of me.

I didn’t have really much of a response to that and between the alcohol and the beautiful girl with her legs wrapped around me, my mind wasn’t really working super quickly. So I said about the only thing that would come to my monkey brain.

“I’m gonna fuck you Anna”

“Thank God”

Now we kissed each other hard. I don’t know what lust tastes like, but I’m pretty sure her kiss was pretty close to it.

I pulled off the crew neck she was still wearing along with the shirt underneath it so she was now just in her panties and a bra. Then I rolled her over so she was laying on top of me. I kissed her, and then moved to her neck. I then reached around and unclipped her bra and let it fall. I admired her body for a moment, then moved in and bit her right on the nipple, just hard enough for her to let out a little squeal and she slapped me on the head.

“Hey!” She laughed “Lick, don’t bite!”

I looked up at her and replied “Don’t forget that yourself.”

Anna was still on top of me with my face in line with her breasts. I started pulling her up my body and kissing down her body as she moved up. Soon I was kissing the area right above her panties, feeling the wetness with my chest and chin.

At this point Anna was basically sitting on my upper chest with her hands on the wall behind me and her pussy just inches from my mouth.

I looked up at her and said

“Take your underwear off”

“Yes sir”

She spun to her right real quick so she was sitting on me like a bench and straightened her legs and pulled her panties off in one swift motion and then spun herself back to straddling my face.

“Full permission to grind your pussy on my face” I said “just don’t drown me.”

She laughed but she did as she was told and picked up her pelvis and moved her pussy up to my mouth.

I licked her labia and teased around her pussy for a few seconds before eventually making contact with her clit. The noise she made in response was akin to someone who had finally got to sit down after a long day.

After that I began to softly suck on her clit as she began to grind her hips into my face.

Anna was absolutely loving that, letting out long, slow and mostly quiet moans, as I felt a pool of wetness forming on my neck and upper chest.

Suddenly I felt her legs tighten around my face and the grinding began to become more forceful. Anna then let out the loudest moan she had so far, as if she had accidentally let this one slip through the cracks. Her legs tightened as her whole body tensed and she went silent and I felt another burst of wetness.

Anna moved her butt back down and sat on top of my waist area and looked down at me.

“You really know how to do that, huh?”

“Shit Anna. You did most of the work”

She smiled and wiped some of her wetness from my chin and then laid down on me and kissed me, then backed off and whispered

“Your turn”

At some point or another I had lost my shirt but I still had my sweats on. As Anna kissed my chest down to my abs, she pulled my sweats to my knees and I stepped out of them and she threw them onto the floor. She then kissed her way back up to my lips as she began to rub my cock through my underwear while we made out.

I’m not gonna pretend that I remember what exactly was said between us in between kisses, but while she rubbed and squeezed and teased different areas of my cock, our best version of dirty talk ensued and it had both of us absolutely intoxicated with lust.

Finally she pulled my underwear off and moved down my body. She gave my cock a sensual kiss on the tip, then slowly engulfed my cock with her mouth as far she could. She then pulled back and spit on it and I swear to you I almost came right as she did that. She began to lick around the base of my cock, getting the bottom half nice and wet, and simultaneously was softly squeezing my balls. Once she was satisfied with how wet the bottom half of my cock was, she grabbed the base and put the head back in her mouth and slowly began to jerk me off while bobbing her head on my cock but only going a little deeper than the head, making sure her tongue spent most of its time on my frenulum.

I grabbed her by the hair and pulled her off me after a very short time of her doing that. I was in ecstasy and easily would have had a heart stopping orgasm had I came in her mouth but I needed to fuck her.

I pulled her face back to mine and kissed her hard. She pulled off me and said “look, if you’re clean we can forget the condom. I need to feel you, and when it comes to my birth control, I don’t miss.”

“Well I haven’t had unprotected sex since the last time I got tested”

“Good enough for me” She said and kissed me.

She was on top of me and lined her pelvis up with mine and began grinding her pussy along the length of my cock.

“Mhmm I need you inside me Sammy”

“What do you say?” I smiled and looked at her

She whispered in my ear

“Please”

We stopped grinding and she sat up and I moved my hips down so she could get up on top of my cock, and then she slowly sat down on it.

The entire time our eyes were locked and she let out another one of those soft slow moans as she bottomed out.

Then she closed her eyes and rode my cock strictly for her own pleasure. I had set out to fuck her, and here she was fucking me. After riding me for a few minutes and through an orgasm or two, she laid back down on me and kissed me with my cock still in her.

I wrapped my leg around hers and rolled her over so I was on top of her.

“Pick your butt up” I said, and as she did I slipped a pillow under her butt. Lucky for me, the pillow was the perfect size. My cock and her pussy lined up perfectly, and I pushed my cock into her she let another louder moan through and locked her legs around me again. I then grabbed her hand and put her pointer and middle finger in my mouth for a second, then told her

“Rub your clit while I fuck you”

The only response I got was a moan as I put my hands on her waist and stood up on my knees with her on her back, legs wrapped around me and my cock inside of her. Then I started thrusting slowly. This position created some of the most intense sex of my life. I started to speed up a little bit and the only thing I got from Anna was encouragement.

“Yes. Harder.” She moaned

Soon enough, with a few more moans of encouragement, I was thrusting into Anna just about as hard and as fast as I could. She was now being loud and not being shy about it. Between me filling her with my cock and her still rubbing her clit, Anna was on a different planet. Her eyes were squeezed shut and the only time she did anything but moan was to give me little whispers of direction.

Suddenly her eyes opened and she looked up at me, and I met her gaze. She used her legs to pull my torso down to meet hers and kissed me. When she did this I had stopped thrusting into her, but in the middle of our kiss she started thrusting her hips from the bottom, encouraging me to fuck her like this too.

Before I could, though, she wrapped her leg around mine, as I had done to her, and rolled herself over on top of me. She found my cock again and slowly sat down on it and began to ride me much softer and more sensually than she had before. We were making out before she pulled back and met me with her eyes.

“Come for me, Sam”

“Mmm oh my God Anna. Where do you want it?”

“Inside me Sammy. Fill me up. Do it. Come for me.”

And that was it.

What followed was probably the most intense orgasm that I can remember having. Now it was my turn to let out a long moan as I emptied everything into her and she continued to ride me before slowly coming to a stop and collapsing on top of me.

After 5 or 10 minutes of making out, Anna snuck out of bed to go use the bathroom. Seeing as how we had both just about fucked the other senseless, Anna was gone for about 30 seconds before I started to drift off to sleep. She could have been gone 5 minutes or 5 hours and I wouldn’t be able to tell you the difference but what I do know is Anna caught my drift when she slipped back under the covers because she snuggled right up next to me and fell asleep.

I woke up to Anna nudging me and shoving a bottle of water in my face.

“Hey. Wake up and drink this. Between the drinking and the sex you’re probably a little dehydrated.”

I smiled at her. “How thoughtful of you”

She smiled at me while I took a drink. Once I was done with it, she took it from me and set it back on the table. Then she rolled back over to meet me face to face and kissed me softly on the mouth.

“I had a lot of fun last night” She said. “I was thinking about this before you woke up, and I think that maybe we should keep doing that.”

I laughed. “What would lead you to believe such a thing?”, clearly not arguing, but more just interested in listening to her verbalize whatever feeling it was she had for me that had come to the forefront last night.

“Well The idea of having to go searching for my next real relationship already doesn’t sound like too much fun to me. I dated Brady for six years. I want to take advantage of not having to take things so seriously. But I’m also not really a fan of meeting and fucking a bunch of new guys. We know each other, we like each other and clearly we have some untapped sexual chemistry.” She gave me a mischievous smile.

“I guess that’s fairly well thought out.” I said, pretending as if her proposition actually required some contemplation.

She then wrapped her arms around my neck and pulled me in for a long slow kiss, seemingly using her tongue to persuade me without words.

“I think I like your idea, Anna.”

Source: reddit.com/r/gonewildstories/comments/ekus3y/didnt_see_this_coming_mf