Passionate friendship with an older woman [MF]

* Preface – So I’ve been a longtime lurker in this sub. I have swayed back and forth on sharing my experiences, but finally decided to start. Not only to share, but also to solidify my memories and spend some time revisiting them in detail. I was only in long-term relationships in HS and Uni. Then, I discovered adult dating sites right as they hit their stride in the early 2000s, and it certainly led to many wonderful memories and friendships.

* I’ve seen a few things that turn people off in this sub, so I’ll be clear here: names will be changed, I’m always safe but mention of protection is left out unless it was important to that encounter, and there’s no reason to embellish as reality was fantasy enough for me. I will break stories apart for brevity’s sake, but never hold follow-up parts hostage just for attention and feedback. They’re coming.

*Season 1 – Lani*

[FM] Meeting a lawyer on craigslist and playing as his niece

Wow, this turned into a fucking long post, sorry about that. Also, this is more sexual than my pizza incident, but not a ton, so if you really want full on sex you should keep looking. This is just another one of my craigslist encounters that happened a few months ago (I’d probably never agree to do this kind of thing in winter, too damn cold).

In his listing, he described what he wanted as something “only for risk-takers” and “real exhibitionists”. I know both of those sound dumb out of context, but when I’ve had a bit to drink and I’m really craving that particular fetish that kind of talk really appeals to me. The post was pretty simple, he worked at a local law firm that had an attached parking garage. He wanted to meet a girl willing to blow him in between two strangers’ cars and maybe then fuck in the back of his SUV. What really sealed the deal for me was that he finished his post by mentioning that there were security cameras in the garage, but he was pretty sure they were just for show. The idea of possibly getting caught (even though I doubted he’d risk his job so they probably were just for show) makes me almost feel like I’m going to have a panic attack, but in a good way so I had to message him back.

Choir Tour [group, cum, cuck]

Ok, this happened to me many years ago when I was in college. I was in the school choir, and we would go on a choir tour during spring break. We would sing in various cities along the way and then have a couple days free at the end to just hang out. That year, we went to Fort Lauderdale. During the last three days, I was rooming with three other guys: Craig, Kyle, and Buzz (names changed for the story). While they were all out on the beach, I was with my girlfriend Gretchen in our room, taking advantage of some alone time. We were completely naked, and she was riding me, when the hotel door opened and all three guys walked in. I was just in the middle of busting my nut inside her when this happened. I wanted to crawl under the bed, but she was on top of me. She just casually dismounted me, and waved to the boys, and said, “Hi guys.” I thought it was weird how relaxed she was.

[MF] First time with wife’s friend [open marriage][swingers]

TL;dr Open marriage, wife sets me up with one of her coworkers, setup only, fucking her in part 2.

My wife and I have been married for 15 years, we’re in our late thirties/early forties and I think we have an incredible sex life and the comfort and trust level is through the roof. Honestly, it’s been pretty damn good since the beginning seeing as how we dated for quite some time before getting married. We had lots of time to learn each other’s bodies, how we each respond to different situations but mostly, we had lots of fun, and lots of practicing fucking each other. One common theme though with our sex life is that we’re always looking for ways to spice it up and I would say things have gotten increasingly kinkier as we’ve matured. We’ve probably dabbled in most of the usual kinks; watching porn together, lots and lots of toys, light BDSM, fucking outdoors but the urge for more never goes away.

My [F]irst Squirter

This story happened about a year and a half ago now. I was 21 and working a summer job out of state and living at my buddies house from May-August. My buddies parents were really cool. They only charged me $150 to live there for the entire time I was there and they gave me a car. Their was only one rule in the house…no random girls. I didn’t have a problem with this because I had a girlfriend who actually visited me there a couple times. Well towards the end of summer we end up breaking up because the distance was too hard. This is when I download Tinder.

Immediately I start matching with some girls most of which didn’t really turn into anything but some, and one in particular, did. A little about me I’m 6′ tall with short brown hair and brown eyes. Athletic build but also about 5 pounds of weight I wish I didn’t have. This girl I match with, we’ll call her Mary was about 5’2″ dark hair very tone body with a little smaller tits but a great ass.

Caught [MF]

Your phone buzzes. You’re busy so you ignore it, but it buzzes again. Sighing you flip it on and see two texts from your roommate. “Having a friend stay over tonight” “He’ll only be here the one night don’t worry” they say. Oh god she’s having a guy stay over, you think to yourself. Though she didn’t often announce her ‘boyfriends’ so this one might be different. Maybe? Work isn’t going to finish itself, better get back to it. A few minutes of semi-frustrated work later the front door opens. I walk in after your roommate and look around, its a pretty big place for just the two of you. I keep talking with your roommate, you can hear a few words here and there “my room, her room” “bathroom to the right” nothing too interesting, you’re pretending not to care. “She mostly keeps to herself” your roommate says. You’re obviously not going to get much done right now, not like this. You get up and head down the hall. As you walk out we lock eyes briefly. Oh he’s cute dammit, you think to yourself. You were secretly hoping you could find a reason to hate me. “Hi you must be the friend staying with us” you say, trying to sound like a nice person would. “Yeah, hi” I say holding out my hand for a handshake. “Nice to meet you” we shake hands, its a little awkward. Your roommate interjects “well why don’t we head back to my room” she says while dragging me gently “its getting kind of late” Is it getting late? Shit I guess it is. It was already 9pm without you noticing. Your roommate and I retreated to her room, you sigh and grab something quickly from the kitchen.

My Two Women [MF] [First Time Anal]

Let me preface this post by saying it is my first real foray into writing anything sexual, and I’m sorry if it’s a bit long!

My Two Women

There are two women in my life. One of them is my wife, who smiles at me as she lounges on the couch with our friends and sips wine while telling us all how she’s going to beat us up and take our lunch money for being so nerdy (I run a DnD campaign and get somewhat less cool from there). She is the perfect image of a brilliant and successful woman whom I love deeply. The other is my slut who lays on the bed with her legs spread, crying out and moaning as I lick her slit and bring her just to the edge of orgasn but avoid sending her over it. She sinks her teeth into the pillow when I take her from behind to avoid screaming and disturbing my neighbors on the other side of too-thin bedroom walls. There are two women in my life, and they happen to inhabit the same body.

[MFMF] [Group] Unexpected Cruise Adventure

**all names changed for sake of privacy**

Longtime lurker here without a whole lot of titillating personal experiences myself. But there was this one time…. Always wanted to share here, but never could be bothered to write it all down. I guess we can thank winter weather and airport delays for finally making this happen:

The story takes place during my final year of medical school. For those who aren’t familiar with the American Med School system, typically our first two years are classroom based, the third year consists of vigorous and brutal clinical rotations, and the fourth year, with the exception of a few mandatory rotations, is largely a choose-your-own-adventure story to allow students to prepare for their specific residencies. After getting ¾ of the way through med school, though, you can bet more than a few students use this renewed freedom to live a “normal” life for a bit again, whatever that means.

[MF] A very special New Years Eve Party – Part 2

Thanks for the great response to Part 1. Apologies for the cliffhanger but hopefully it will have been worth the wait. [For part 1 please click here](https://www.reddit.com/r/gonewildstories/comments/5n5d08/group_a_very_special_new_years_eve_party_part_1/)

Part 1 ended with Sarah grabbing my hand and leading me out of the sitting room leaving my wife Gemma, and her husband Matt behind. As we passed the kitchen she grabbed a bottle of fizz from the fridge and we headed upstairs. ‘It’s a home fixture for me’ she said as she led me into her room. Suited me as she and Matt had scored the master room with a huge super king bed and ensuite.

I opened the bottle and poured us a glass each, there was a slight air of who is going to make the first move. But as Sarah took a swig from her glass she pushed me over to a chair and told me to sit down. She took my glass and put both of them down, pulled her dress up and straddled me. ‘Now where were we’ and with that she leant in and kissed me. The kiss was very different from our first one a couple of hours ago during the game. This was much more passionate with our tongues darting in and out and our hands exploring each others bodies.

Threesome weekend [MFM]

A few months ago I shared a story of a failed threesome with my buddy and his GF on this sub. I received a lot of negative feedback due to the fact I had a SO at the time and was cheating. I have since parted ways from the girlfriend and after several months the opportunity for another threesome arose. This is that tale. Names changed of course.

This past weekend found me crashing Saturday night at Mike’s house so we could get an early start on our first skiing trip of the year. I arrived about 9pm with two six packs and the intention of kicking it and drinking some beers. Mike and I cracked the first brews and sat in the kitchen catching up on the usual business, when Molly appeared naked in the doorway. Molly is about 5′ 3″ 115lbs with tiny tits and a firm round ass, a very athletic build.

We spent about 90 minutes just chilling at the kitchen table polishing off the 6pk and talking about everything from the mundane to the more risqué. I had a gentle buzz going from a couple high ABV craft beers when I excused myself for a cigarette. I returned quickly from the Arctic blast that was outside and found the kitchen deserted. The fun part of this story starts right about here.