I guess I just love older women [MF] [cheating] [MIL]

Truth be told, there is nothing to “guess” about here — I know I’ve always loved older women.

Don’t get me wrong, I love my wife as well. She is a fit, big breasted brunette that never fails to turn heads. Her *mother* though!

My mother in law is a little bit taller than my wife, maybe 5’6, and thin. She isn’t fit as much as she is just one of those women that hit the genetic lottery and has remained slender throughout her life; at 55, she could easily pass for 45. She is divorced and lives alone, and in the years prior to this story she had undergone something of a metamorphosis. Call it a mid life crisis or her finding herself, she suddenly started dressing in skin tight jeans and revealing tops.

It all started with a vintage Mustang.

Key West [MF] [FF] [MFMF]

Late 1986. Reneé woke up sick the morning that the test results would come out to find out who made First Class. Pulling the covers over her head she said, “I’m calling in sick”.

“Get up, let’s go for a run”.

“No”

“Wanna fuck instead?”

“I think I fucked myself on that test. The more I think about it the worse I believe I did. Plus they are only advancing the top three percent”.

“Bullshit, you passed. No one knows the paperwork better than you. The Chief over at Base Admin calls you instead of reading through the books”.

“I didn’t pass. I won’t ship over again if I don’t make it”.

“Yes you will. Come on, let’s run. I’ll even keep up with you”.

“You can’t”.

“Let me rephrase that. I’ll try real hard to keep up with you”.

Begrudgingly she got out of bed and got dressed. After stretching we were on our way. She set a brisk pace. We ran silently for a few miles before she said, “I’ll meet you back at the house”, then started to outdistance me. I didn’t even try to catch up.

Stacy’s Night Out Pt.1 (FF)

For the second time in the evening Stacy felt a hand on her knee. Her brain was a little fuzzy after downing a margarita and a beer within the first half hour of arriving at the bar but she needed something to strengthen her resolve. After some badgering she had accepted the invitation from the office cool kids for a night at their favorite watering hole.

Working with people that were 10 or even 20 years younger was taxing at times, sometimes Stacy felt like an anthropologist observing a strange new tribe. She had heard bits and pieces about their Friday outings around the office but she had dismissed it as youthful bragging and one-upmanship. “These kids have no idea the things I’ve seen,” she frequently thought to herself.

The first hand on her knee was from Vanessa, the queen bee of the group. Stacy had written it off as the overfamiliarity of the sorority girl type. It seemed to go along with the effusive greetings and constant hugging. The hand never went anywhere and Vanessa moved on soon to flit about some other beautiful person.

[MF][F] one year to this day my wife and I had our first and only threesome.

It was a Sunday night and my wife and her friend decided to go out drinking. We have always had an relationship where if she wanted to be with someone else she has my blessing. I stayed home to play Xbox and would get updates via text every so often. Being Sunday night not to many men at the bar. So to spark things up I decided “ I will send a dick pic to my girl.”
What I didn’t know was that my wife’s friend had her phone. After some mild embarrassment and flirting I convinced them that they needed to kiss. And so they did. And giggled. Then they got more drinks and I convinced them to kiss each other in the car, which was surprisingly not that difficult to do.

Fucking My High School Bully [Str8] [m/f] [prost] [Mdom] [reluc]

Blurb: *After years of torture at highschool, James or ‘Little-Dick-Jimmy’ gets his chance to make all of that time worth it by hatefucking his former bully.*

**Author’s Note:** *This is a story of rough sex and ‘hatefucking’. It is in no way a non-consensual story. I wanted to clarify this because I realise there are certain parts may seem like they’re hinting at a rape scenario, but that’s not the case at all. If rough sex, dirty talk, mild violence or hate-sex disturbs you, please do not read on. Otherwise, enjoy.*

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I wasn’t a popular guy in school. I was never any good at sports, I froze up when talking to most people, especially girls and I much preferred keeping to myself. It didn’t help that I was your fairly stereotypical-looking, geek kid. I had to wear braces throughout most of school, I was slim and fragile, and my bright Orange hair was fairly long and very curly, so I definitely stood out in a crowd. But hey, I didn’t have bad acne, so, I guess that was something.

Swapping Partners With The Neighbors [MF] [MF]

My wife and I have a very active sex life and have brought other women into our bedroom before. When we first started seeing each other we both agreed on a rule that the only way we could have sex with another is if we agreed and could either participate or be there while it happened. We have talked about another sharing and swapping with another couple and last weekend we had that chance.

We see our “neighbors” , they actually live two streets over, fairly regularly when we are walking around the neighborhood or at the pool in the summer. Adrian and Carrie are their names and we always talk and are friendly when we run into each other. Over the past year we have become closer and been to each other’s house a handful of times for rinks and dinner. Adrian and Carrie are both about the same age as we are, right around forty.

Playing with my professor and his wife. [FMF]/[FFM] (Part 2 of 2)

[<— Part 1/2](https://www.reddit.com/r/gonewildstories/comments/7tpp9c/playing_with_my_professor_and_his_wife_fmfffm/?ref=share&ref_source=link)

—START Part 2/2—

Turning around to a surprised and sexy David, I leaned upward against him for a heated kiss too. For a few seconds we stood there, in our pajamas looking intently and excitedly at each other. The mood was electric and energized. David then said, “Jen, you don’t know how long I have wanted to do that.” I said, “What do you want to do now?” not knowing how to continue on from here. Tricia responded, “I need to know that you are choosing to do this, and that you don’t feel pressured.” I nodded my head enthusiastically. David followed up and said, “I think you should take your clothes off now, Jen. In fact, we are all overdressed right now.” He closed the door to the room and gave me a mischievous look, locking the knob in case Jessica woke up and tried to come in. He continued, “But first we need to talk shop. What is your birth control situation?” I told him I had a copper IUD. He then asked if I have slept with anybody recently and if we used condoms. This was all very normal to me, since I go through these types of questions with people before I am sexual with them too. I told him for the last few months I have been hooking up with this girl from one of my classes, and at the beginning of the semester I had a fling with two guys who were roomates at the same time, using condoms, also assuring them I was clean and had no symptoms of anything. Tricia told me I had nothing to worry about as they were asymptomatic, and they always used condoms when being with new partners during swinging sessions. David then said, “We trust you Jen, so it is up to you if you want me to use a condom.” Immediately, I said, “Let’s do it without! I want to feel everything.”

Playing with my professor and his wife. [FMF]/[FFM] (Part 1 of 2)

[Part 2/2 —>](https://www.reddit.com/r/gonewildstories/comments/7tppor/playing_with_my_professor_and_his_wife_fmfffm/?ref=share&ref_source=link)

—START Part 1/2—

This story has a lot of backstory and build-up, but I promise you it is worth it and will make it that much better and beautiful.

As I have written before, I have always been a sexually adventurous person. I started experimenting sexually at a young age with another girl I was close to. At the age of 15, I lost my virginity to a boy who was 18. I identify as bisexual and have always been that way I think. Both sexes turn me on pretty much equally. My parents raised me in a very open and free environment, but demanded responsibility and self-ownership. My mom was very sex-positive and educated me well on all things sex related. Interestingly, they were okay with me having boys and girls in my room privately, even overnight. I guess they figured that it was better if I was not sneaking around behind their back and felt safe and comfortable. Throughout middle school and high school, I had sexual relationships, which may appear abnormal, but it was not to me. Once I started college, I became involved in the group sex scene. You know, like orgies and swingers parties, often referred to as “the lifestyle.” One might think that such events are risky with disease and all, but these concerns are taken very seriously. At events, protection must always be used. Not that I would participate in group sex all the time, but I did very much enjoy it. I love meeting new people and exploring with them sexually, and making them feel good.

I’m the world’s worst boyfriend (or at least I used to be), [mf]

This is my first post, and I have a lot of stories to tell. (all true). Some funny, some sexy, some lucky, and some strange. If you enjoy this at all, please let me know. And spoiler alert, monogamy is difficult for me. I probably need counseling, but you aren’t going to convince me to get it.

So the back ground story today, is me, dating a girl (A). She has her best friend (T). T is my ex girlfriend. We had dated a year earlier but never slept together. She broke up with me, I started dating A, end of story (almost). I worked with T’s mom, and T’s mom had a friend (R), whom also worked with us, and subsequently was the downstairs neighbor of T and her mom.
I was in High School, 18, senior year, and I had a perfect routine. Go to school, get out at 3, tool around for a bit, sleep with girlfriend at her house, then go to work for 5 hours, go home and then do it all again the next day. One day though, I see T in the halls at school and she asks me how me and A are doing. We talk for a couple of minutes and she tells me that she regrets breaking up with me, “mostly because we never got a chance to fuck.” Mr. non monogamous was developing on this sunny day, and I respond that I’d be happy to stop by anytime to fix that, but I make it clear that I’m not breaking up with A just to sleep with her. She says “stop by today after school”!

My First Orgy: An Awkward Teenager at Tommy Lee’s Sex Mansion [Group] [Attempted]

“The lunar eclipse is this Saturday, Eddie, and my friend is having a naked party,” she said on the phone. Tara’s father was a famous musician from England, which made Tara a socialite. Once, her British rock star father and I sniffed cocaine off a skull key in the bathroom of Dublin’s. Everyone knew about it, and my popularity skyrocketed as a result.

“Is Manson going to be at this one?” I hoped the answer would be yes. At the last party I had gone to with Tara, a Tuesday night thing, the goth musician Marilyn Manson had left an impression on me. It was in regards to a joke he had made about men and women who stare at their own fecal matter. According to Marilyn Manson, doing so was a characteristic of homosexuality. I had this nagging feeling in the back of my head, secretly wondering if the reason I got bored while having sex with Rachel had something to do with the fact that once or twice I had stared at my own poop.

“No clue if Marilyn is going to be there, Eddie,” said Tara in that drowsy affectation of hers. She was on first name basis with hordes of celebrities. And she was asexual. “But you still want to have an orgy, right?”