Surprise anal – and I loved it [MF]

This happened a few days ago between me and my boyfriend, Austin. We’re both 18 years old. He’s 6’1” and lean, while I’m 5’4” and a bit curvier. I have a decent rack, 32DD, which he loves, and he’s pretty well endowed, especially when you compare it to how small I am. We’ve never measured it but I’d say 7”, and reasonably girthy. It’s the perfect size for me and sometimes even a bit much. Regardless, I’m one for adventure, and I wanted to experiment with anal. I had just convinced him to try it, and I fucking loved it. The first time was gentle and loving, which was amazing, but I like things a bit more rough, and I mentioned this to him off-handedly a few times. This is the story of the second time he fucked my ass.

We were both hanging out at my house, trying to squeeze in as much time together before we leave for college. We were cuddling after round one, his hand squeezing and kneading my ass.

“I’m still hard, you know,” Austin said, looking at me then glancing at his still erect cock. That’s the one thing about him, he has an insane amount of endurance. I rolled my eyes at him.

[FM] Lovebirds, Ep. 4: Creampied at H&M

So yesterday r/Myhsam and I had a great time. 

It started out with waking up and cuddling in the morning. I was on my back, he on his side, one arm across my stomach. He started to lazily play with my nipple. I love it when his hands travel all over my body to caress me and so I squirmed a little and made content purring noises when his palm travelled down towards my navel. After a few minutes of him lightly stroking my body and me enjoying his touch, he shot me an amused look and said: “You have quite the twitchy pelvis. Is my kitten in heat?” 

He was right. I hadn’t even noticed but I had started to gyrate my hips, subconsciously wanting him to touch my pussy. So I breathed “Yes, yes I am” as he chuckled and cupped my vulva with his hand. His middle finger started to stroke my slit and was greeted by slippery proof that, in fact, I was horny as hell. First he placed two fingers on my clit and started to rub me but quickly found me to be so wet that he slid his fingers down and into my pussy. I moaned as his fingertips started to push against my g-spot and then did the “come hither” motion. Whimpering, I moved my pelvis rhythmically, knowing that this wouldn’t take long at all. Then he took my nipple in his mouth, sucking it at the same time and I just melted in a puddle of pleasure, my pussy spasming in orgasm around his fingers. 

Dared each other to post – seducing my older brother’s [F]riend on a family vacation from [M]y POV [MF]

So this happened a few weeks ago and I still can’t believe it happened. This first post is mostly build up, and somehow got really long, so if you’re looking for a quick release wait for part 2 or SPOILERS read [Brooke’s point of view](https://www.reddit.com/r/gonewildstories/comments/968rt2/my_sexual_reawakening_a_whole_night_of_fucking_my/).
(or for the best experience read this and her point of view simultaneously to transcend all gender into a higher realm of sexual enlightenment)

Quickly about me: I’m tall (6″2), tanned with dark brown eyes and hair and a bit of a stubble, with a naturally muscular body that I really don’t deserve. I’m very reserved, communicating best with cheeky eye-crinkle smiles and physical contact rather than having all that much to say for myself.

Recently, I’ve been going through an extremely messy ending to a long term relationship, and long story short after we broke up we kept seeing each other on and off for a few months (classic). Eventually it became obvious that it was just hurting the both of us. One Friday we called it a day. At that point, I was more relieved it was finally over than anything else.

[MF] Fucking my grad school classmate [cheating]

When I first met Kendall, I hated her. I thought she was the most self-centered, stuck-up, narcissistic girl ever. What made it worse, was that we had assigned seating for three of our classes, and she sat next to me. She would randomly write notes down and slide them to me – some making fun of the teacher, others asking what was happening in ECON, and shit. ECON was a piece of cake for me – I took like ten ECON classes before, but this was her first. Then, as stupid as it sounds, it all changed when she touched me.

I got there early to class, and -crap- she was there early too, so I pretended to enjoy some bs small talk with her while waiting for everybody else to get there, and she did this thing girls do where they laugh and touch your arm or whatever when you don’t say anything that’s funny, and then I knew. This chick liked me. Before going to the gym that day, I quickly instagram stalked her, and found out she has a boyfriend that’s in the Peace Corps or some crap in some foreign country somewhere. I also saw some posts of her working out, and she was pretty toned for a girl. Respect.

[MF] I fucked the Cougar again, this time without Barney.

[first post here](https://www.reddit.com/r/gonewildstories/comments/91jxv1/mmf_i_banged_a_cougar_last_weekend_and_it_was/)

I stupidly left Ashley’s house the first time without getting her number, and I thought it might be kind of weird to ask Barney for her number, so was just going to play it cool and wait until Barney wanted to hang out with her again. That would have been shitty though, because I literally dreamt of her pussy.

That is until Sunday night, I got a facebook request from Ashley with a message – “Hey, had a good time the other weekend – Ashley”. BAM. I was in.

We started messaging back and forth over facebook, then she gave me her number and said she needed to put her kids to bed. I really wished I could have fucked her that night, but she had the kids over the weekend. She said they would be gone Monday, though. Some of you were asking for pics of her, and because I don’t want to put her actual pics up, [she looks like this chick here](http://blog.pinkworld.com/classy-blonde-milf-jewel-posing-in-sexy-black-lingerie-16216.html#&gid=1&pid=3).

So Monday morning comes around, and when I wake up, I get a text, “Dreamt of your cock last night. Can’t wait to see you tonight…xxx”. Holy shit, she dreamt of my cock too? I thought I was the lucky one here to be banging this cougar. I guess it goes both ways. So I respond…

[MF] Fucking My Waitress- for the last time.

**I’ve written about fucking a waitress i met in a couple of other** [posts](https://www.reddit.com/r/gonewildstories/comments/8uz34k/mf_fucking_my_waitress_today_with_pictures/). **This seems to be the logical conclusion to that story. I’ve realized, now that i’ve read through it, is dark as fuck, and isn’t really the sexy sexy sex time that this sub is looking for. Also, if i’m being extra honest I’m pretty hesitant to post it because I know it’s not going to get many up votes, but I want to be true to my experiences. I still really wish** r/realfuckingemosex **was a real thing. But it’s real. Sex for me, great sex for me, the sex that I remember and care about, and shapes me and changes me, walks that impossibly thin trail between pleasure and pain. Sometimes, more often than not, that sex tumbles of that trail and we find that it just pain and when we finally stop falling we realize the experience has changed us. Sometimes for the better. Sometimes for the worse. It’s too early to know here, but goddamn I hope it’s for the better this time.**

Fucked a Random Girl Off the Street [MF]

To start I am 6′ 4″ male and I work out regularly. I’m muscular, tall, and we’ll kept. I’m more confident than your average person. When I walk into a room I like to think I am the most attractive man there. It may not be true, but the confidence has gotten me into a lot of fun situations.

I was visiting a city and staying in an Air BnB. Without my knowledge it was an apartment where the owner (male) was also staying in the other room. This was a bummer, but I decided “fuck it, I’m still bringing back ladies.”

I was walking down the street and I see a girl that I think is cute so I say “Hey, I’m Vince, what’s your name?” She responds with her name and we begin to chat. This is a classic move by me, simply introduce yourself with confidence and start asking a lot of questions like you’re very interested in their answers. We chat for a bit on the street and I ask her if she wants to go to a nearby bar, she agrees.

How to solve a problem like Elena? [FF][Part 5]

Now while it was mentioned in one of my previous stories, I used to rent an awesome little annex. I’m sad I don’t live there now! It was slightly connected to the main house but no entry through it. It had a private entrance and private drive and it’s own walled garden. The actual annex was a white washed building that used to be a small barn. It only had three rooms, the bathroom, walk-in wardrobe/laundry room and the last room. Kitchen, bedroom, living room that was all! Basically, my bed in the middle of the room with the kitchen off to one side.The setting and outside were amazing and whilst the inside was lovely it was less than practical.

I parked up and led her into my garden and up the path to my annex. Once inside I flicked on the lights and tossed my bag onto the floor “Can I get you a drink of anything?” I asked trying to break the silence she just shook her head “You can take a seat on the bed if you like? I don’t really have room for chairs.” I tried to smile at her as she perched on the end of my bed with her bag on her lap.

A favour led to fucking an old [f]riend on a hot su[m]mer day and satisfying a well buried desire.

A hot summer day, the climate change seemed as undeniable and arrogant as arguing with thermometers. A shimmering and merciless heat. The grass and most plants died during the recent heat period. The cold beer cooled the calluses on my hand – created by the unrelenting garden work of the last days.

They moved to a new city. The salaries are way better they said – inscrutable to me, how they could think about work while living under a burning sun we got this summer.

I selflessly offered my help to dig over their garden and remove most of the dead plants and trees. The house they moved to, still seems more like a burden than a home to me – but who am I to judge.

There is an all surrounding smell in the air. An old familiar mix of burned skin, cut grass and dust. It reminds me of earlier years when life was careless and easy. Thoughts would never escape to the next day and the hangovers where sweet and not dreadful and lasting several days.

[Group] I had a lot of fun with my (f) exhibitionist friend, her (f) roommate and a phone’s camera

So after a couple of really wild nights doing lots of dirty things in some kind of orgies, Nat and I wanted to go back to the basics. But the basics for us implies someone watching us, so she asked her roommate Vicky if she wanted to join us. Of course she said yes. Who wouldn’t want to have that kind of fun and pleasure we know we have enjoyed until now? One thing we decided was not to get high or drink alcohol, you can’t abuse MDMA, specially.

I told them that one of the things I enjoy most from my exhibitionist kink is take sexy photos of myself or (much better) let someone take them. Vicky said she also loved to be photographed by someone while she gets wild.

Nat said to me: “Would you like to take pictures of the both of us?”. She looked at Vicky and they both smiled. Nat gave me her iPhone, which was the best phone in that moment.

And they began to pose and to pull up their shirts while I was taking photos of them. At first it was just fun, they were doing silly things and we were all laughing, but soon, when they took off their shirts they were feeling more sexy and I was really enjoying watching them.