All right everyone, let me tell you about the time I lost my anal virginity. This happened just over 24 hours ago with my [22/F] boyfriend [29/M] of a few months. For some background, he has had anal sex before but I hadn’t ever – only some light anal play, maybe a finger on occasion, that sort of thing. For some of the cute background on our relationship because I’m sappy and have an emotional approach towards sex, we’ve both said one of the main things that attracted us to the other is that we’re both equally goofy and silly. We joke around a lot and have a lot of fun teasing each other. I have a tendency to be a tad bit high strung while he’s very mellow, so we balance each other out nicely. All in all, he’s fantastic and last night only proved this more.
Tag: Girlfriend
Girlfriend’s Engaged Friend [MF]
Long time reader of these, I recently had something happen that I think deserves a post. I briefly posted some pics from the other night, but here is the backstory and more photos.
Apologies for any typos, I wrote this quick and didn’t have time to proof read as the story is ongoing…
My girlfriend and I have been together for about 5 years now. I’ve never cheated and until recently we’ve never even talked about any sort of “open” relationship but that all changed this week, when her friend Kat came to visit. Kat is one of her best friends, they’ve known each other since middle school and thus I’ve known her for a few years as well. She lives on the East Coast, but she’s come to visit us before and it’s always a lot of fun. Aside from being a very cool girl, Kat is a total smokeshow. She has a really cute face, small (but very perky) breasts, and a 10/10 ass. The ass doesn’t even make sense, she’s got such a skinny waist and then all the sudden WOW…there’s a perfectly round bottom.
A nice hotel room right there, and I’m relegated to the stairwell with him.. [MF]
So I’m kind of an oversexed chick. My husband and I go to sex clubs and do couples stuff, and I let him have a girlfriend, which turns me on. He knows I fuck around too, but he doesn’t want to know about it. Recently I went to Chicago on a work conference and knew it was a great opportunity to do some fucking around. I wore a dress that barely covered my tits, which I completely love, and went running around the city like a little slut. The first night I made out with a guy at a bar, but he wasn’t up to my standards to bring him back to my hotel. Second night, no luck either. The third night I finally found somebody on Tinder that I was into, but unfortunately my friend had come up from Ohio to spend the last night in the hotel with me. I secretly texted him all night while I was at the bar with her and when we got back to the hotel she passed out pretty quickly. I mumbled something about going out for Tylenol and went downstairs barefoot, still in my dress.
Flying solo? Why not… [MF]
If you’ve read the rest you’ll know that the progression hubby and I have made into an open relationship has been fast and furious. In the past months we’ve gone from threesomes, to group sex and have managed it all very comfortably. It’s been uncomplicated, with no dramatics, and to be totally honest, not even a disagreement between us. We just get each other.
I have a fantastic opportunity to learn some gardening tips from one of our friends from the previous stories, Matt, but knowing myself I am certain if his cock comes out I’ll be on my knees in a second. So, I do what any horny wife would do and ask hubby what he thinks before I make the plan. We don’t play alone and although we’ve talked about it in general it’s never come up in this context before. As always he says (as I would to him), “Do what makes you happy, and what you’re comfortable with.” So off I go to have an afternoon with Matt.
To read our other stories and get to know us better before you move on, read these first: [The Cocks and the Guac](https://www.reddit.com/r/gonewildstories/comments/5zc100/the_cocks_and_the_guac_our_first_group_experience/) and [If you swallow, it won’t get in your hair](https://www.reddit.com/r/gonewildstories/comments/61so0o/if_you_swallow_it_wont_get_in_your_hair_grouporgy/)
seducing him to cheat [fm]
I remember when I first met him about a year and a half ago. We’ll call him Chris. I asked my friend, Stephanie, about him and she proceeded to tell me he had a girlfriend. I remember being kind of sad, but obviously, I got over it. We got a lot closer this year, though! Me and Stephanie began to hang out with his roommate a lot.
In February, Chris told Stephanie’s boyfriend that he thought I was hot. So then, over spring break, me and Chris kind of started texting and snapchatting, and I was pretty sure something was going to happen between us. But when I got back to school, he kind of randomly just stopped talking to me. Found out a few weeks later that he was getting back with his ex girlfriend. They had a really shitty relationship and have both cheated on each other multiple times, so I was a bit confused, but whatever. Last night, we went out with him and his roommate. As me and Stephanie were getting ready, she turned to me.
“You know… I bet you could get him tonight.” I laughed and glanced towards her, narrowing my eyes.
Bianca in Berlin – Part 1: Alex the Barista [MF]
The name’s Bianca. I moved to Berlin, Germany earlier last year for a job at a start-up. The timing was perfect – I just broke up with my emotionally abusive boyfriend, and decided to take time out from serious relationships to heal myself.
A little intro about myself; I am 23 years old, I am about 5′ 8, dark brown wavy long hair, big brown eyes, C cup boobs, long legs and a big butt for my figure.
Story: I like Berlin for its coffee culture – lots of cafés around, and for a newbie in town like me, it was a great way to make friends outside work.
Since my work is mostly based online, I can do it anywhere with an Internet connection. So I started coming to this coffee shop in Berlin Mitte that serves amazing Americano and very reliable Wi-Fi.
I had my eye on this tall and handsome barista called Alex from the very first time we met. He’s about 6 ft and had this athletic build with tattoos on his right sleeve with messy blonde hair. He has the most amazing blue and green eyes I’ve ever seen. I didn’t have the courage to make small talks with him so all we did was exchanging long and intense gazes.
[MF] Started from my own hand, finished in someone else’s mouth
To start this story off. I’m gonna say right off the bat, I’m a nerd, a 19yo gamer geek, have no girlfriend also never had any sexual encouters with anyone, until two days ago.
So, few days ago, my sister told the family that her old friend that she spent 5 years at the University will be coming and staying at the house for a few days. I could see how excited they both were to see each other because they were chatting on the phone every single day. She showed me her picture, what I was just a 5’9 girl with a face full off pimples and a nerd glass on her eyes. Nothing too special, except that she have quite a hot body.
So days past, until the day she came to my house which is almost a week ago. As a gamer, what else daily other than sitting alone in my room with a ps4 controller in my hands. From up in my room, I heard some excited screams from downstairs, I knew it was the girls. So excited meeting each other. Since I’m a social kind of guy, I stayed there refusing to go downstair and greet myself.
[MF] My Girlfriend’s Adventure
So, a few months ago, maybe even a year ago, my girlfriend (who I shall henceforth refer to as Rae) and I, both of whom are now 24 and were at the time of this story 23, agreed to have an open relationship. Although the relationship is somewhat open, we still have fairly clear boundaries:
+ No fucking each other’s mutual friends
+ No relationships, only casual sex
+ No indiscriminate fucking, we have to tell each other every time we fuck someone.
+ Lastly, we can’t fuck any more people than the other person. That is to say, every time I fuck someone, I have to wait until she fucks someone and the score has been balanced before I can fuck another person, and vice versa.
That might seem restrictive, but actually I would argue that it gives us more freedom. But that’s a deeper philosophical topic, and I don’t really wish to discuss philosophy here. We also agreed that we would both wait for me to fuck another girl first, since we both agreed that it would be much harder for me to get laid than it would be for her to get laid (thus, we would avoid a situation in which there would be an extended period where one of us has had sex with someone else while the other person has not).
[mf] The bet.
‘I bet I can make you cum in less than 5 minutes…’
Another true story from university days. I’m 19, sitting in my friend David’s room at Cambridge university, and we’re chatting about sex. David has been one of my closest friends since we were little kids, growing up in the same village. We went to school together, primary then secondary, and though we hung out with a big group of mates we would probably refer to each other as best (opposite sex) friends.
Despite this, we had never been a couple. People would say ‘seriously why did you guys never get together, you’d be great’, but we never did. I don’t really know why, there’s no single reason. We both went out with other people through school, neither of us really seeing the other as a potential partner, but we stayed close and shared secrets just the same. We are still close friends to this day.
People would also ask ‘doesn’t the sexual tension between you guys just get unbearable?’ It didn’t, for the simple reason that we had, on a couple of occasions, had sex. Nobody knew, not even my closest female friends – it was our deepest mutual secret.
[MF] My first “older” woman
A few months after I “became a man”, I was home from college for Christmas Break. I was working for a property management company owned by a friend’s father, and assigned to a project at an old mill building that had been renovated in to condos. The management company had reached a deal with a local ISP to be the provider for the building, and now were running CAT-5 to all the condo units. (Late 90s)
I was in one unit, covered in dust and sweat, installing the box in the wall when the owner started asking about computers. She never had one at home, and figured she should get one since she has Internet.
Being a computer guy, I was happy to answer her questions. It soon became obvious she didn’t have a clue, and she finally asked if I would go to the store with her, to make sure she didn’t get scammed, and she would pay me for the help. No problem, I figured. We decided to meet Saturday at the local big box store.