Couple small notes: It’s now been 2 months and 5 days. As for the double penetration, it is happening tomorrow (I am excited!!). We are all traveling from the holidays today and I want to be able to take our time and not feel rushed.
Category: gonewildstories
[M]y wi[F]e is beginning to embrace her sexuality
I’ve posted before about some of my experiences both with my wife and with other women. She has some health issues that make having a reasonable amount of sex difficult for her. But we started working with an anti-aging/functional medicine doctor in another state who is excellent and we’re both getting stronger and healthier. Her, modestly better. Me, I’ve gotten dramatically stronger and re-energized, which is a bit of a problem. My sex drive was reasonably high before, now it’s getting back to where it was when I was in my 20s. We’re in our mid 50s now.
But another issue I never wrote about here was her sexual inhibitions. There were/are a lot of things I’d enjoy us doing that she wasn’t comfortable with. For example, she had a strong aversion to the word and concept of “fuck” or “fucking”. She viewed sex through the lens of “making love”. Well, sometimes I enjoy making love, having sweet, gentle, loving sex. And sometimes, I want to just take my woman and fuck her deeply, roughly. She didn’t want that. When we first got together and started having sex, one time I asked to do it doggy style and she said she didn’t enjoy having me enter her from behind, it felt unpersonal and cold and dirty to her. Ugh. So we worked around it and I found other women to satisfy some of those needs.
[MF] Ski bunny memories
This all happened about 10 years ago.
I grew up in an East Coast state with a big ski culture in the mountains. A friend’s family from college owned a nice house at one of the ski resorts and he had it for a weekend between Christmas and New Year’s. Since I was only an hour drive away, I got the invite.
It was fun group of myself, my friend, his girlfriend, two other couples, and his girlfriend’s younger sister. Most of us were early 30s, except the sister, Stacy, who was 26.
We all showed up sometime during the day Friday. Some got in a few runs, but we largely met at the house then hit the downtown for dinner and drinks.
Saturday morning was rough, but most everyone got up to hit the trails. I don’t ski, so I slept in and then rented snowshoes. Because I lived local and also work part-time doing catering, I offered to collect money and make a big dinner for everyone.
I Fucked to close a Business Deal, and I got Screwed [MF]
Yes, both ways.
I’m a woman who works in a male dominated industry. Part of my job is to poach top talent from one firm to another. I’m a recruiter, so long business trips, life on the road and putting up with a lot of bullshit. Being a woman helps… as I often trade sex to close a deal. Most of the time, it works. But this time, it didn’t
This year, I met this potential recruit. He’s a big deal and would have been a total coup for me, if I closed him. Normally, a firm would send a delegation of a team to pitch him. Fancy spreadsheets, large signing bonus, wine and dine, all that. My company tried and failed to do that. He gets pitched all the time. Again, big fucking deal.
By chance, I ran into BFD at a conference. He’s the type who “appreciates” a young pretty woman. Normally, BFD would brush me aside. Too inexperienced, too stupid, etc… But when you wear a short skirt and a push up bra, that buys you some more time to pitch. That was enough time to get another meeting with him. Fuck, I’ll take it. The commission check on him alone would be enormous.
Vacation with my bf and his best friend [MF]
A little backstory. I am a 23 year blonde who is very outgoing and loves to make new experience. My boyfriend and I have been together 5 years and this is the story of how I ended up fucking his best friend on vacation.
Earlier in the year I went to Cuba with my boyfriend Adam and his best friend James. The three of us have always been very close. We would hang out all the time and James would often crash in the bed with us after smoking or drinking. So one day we were all on Adams bed talking about how we should go somewhere hot before the holidays. We googled around, found a cheap flight and hotel so we booked a 6 day long trip. We were so excited we started packing the next day.
Now to be honest I have always been attracted to my boyfriend more than anyone but his best friend has always been hot to me. I was excited to pack all my skimpy bikinis and shorts.Low cut shirts, my boyfriend liked to show me off anyway.
The Day I [M]et the Love of My Li[F]e
No one expects Tinder to generate any kind of quality connection anymore. I [M] certainly didn’t. But I’d been divorced for two years, hadn’t had ANY intimate contact for longer, and the bar scene looked like an STD slideshow in a high school health class. So, I gave in and put that iconic fire icon on my home screen.
I knew to manage my expectations. The internet was very clear: being a guy trying to get a date on Tinder is almost as difficult as trying to become a professional athlete. So, I didn’t get my hopes up.
But soon it became a game for me. If I were a hammer, puzzles would be my nail. Learning the best Tinder-game strategy kept me going back, kept me swiping even when I never matched. For example, I knew that I couldn’t compete on looks alone. But if I showed some personality in my pics, my probability of catching a lady’s attention would bump up. Thus, my main pic was me pointing over my shoulder at Christmas decorations in a store with a” WTF” look on my face (it wasn’t even November, for godsakes!).
It turns out that was a winning strategy.
HOW I BECAME A GIGOLO [MF]
Hi it’s my first time posting on Reddit so please go easy on me .
This event happened a while ago and I thought about sharing it .
I am based in Kerala which is a small state in India .
I wanted money to travel the world and was ready to take up multiple jobs . I posted ads on Locanto , Tinder and other dating websites . I never got any request so I just forgot about all ads as I thought no one will want me .
I started to take tuitions for kids in one locality and this is where the story really begins .
One day I got a call from my students mother (first client) she wanted me to provide tution for her son and her daughter , she looked like she was in a late twenties , never bothered to ask her real age . The kids informed me that their father used to travel a lot and rarely used to be home .
[FM] I sucked two of my brothers friends off at the ugly Christmas sweater party
It was a busy family holiday gathering. We were all joined at my moms place, when my brothers two best friends came by….. after everyone had ate, I winked at Joey and he winked back, I pointed to my guest room and he followed…… when we made it in the guest room he was already pulling out his cock as we walked in the door…. his other bro, Blake was already in there stoking his cock to porn on his phone… how convenient, there were two cocks dangling in one room so I decided to have some fun …. both guys sat down on the bed side by side and looked at each other while they smiled…… I started to deep throat Joey first because he was the good boy who followed me in first! As I slobbed all over his cock I noticed Blake start to stroke his dick harder…. so I went over to his cock and began to suck hard while I stroked joeys cock……. then I told them both to stand up and began to rub both of their cocks together as I put both of them in my mouth at once ! Mmmmm…. I sucked the tips of both of their cocks at once as the moaned loud….. I heard a knock at the door… “ yes?!” I yelled…. “ have you seen Blake?” My brother asked through the door….. “no “ I yelled as Blake began to shoot his cum all over my ugly Christmas sweater ….. Joey then grabbed my head and began to push it down on his cock …… both guys taste good…. but I wish I could have taste both of their cum together
[M]y [F]amily Trip to Hawaii
I apologize for the length of this but I had to get it out there!
My wife and I were on a trip to Hawaii for the holidays and we decided to invite along her parents, her sister and husband. We all split a 3 bedroom condo with 1 room having an ensuite and the others sharing a bathroom in the hallway between the 2 rooms. As you would expect with a family trip it got pretty difficult for us to get some alone time.
My wife is a 5’8″, 130lb brunette with a small C Cup. She’s fairly fit and frankly way out of my league. I’m your typical 6’1″ blonde dad bod with a chest full of hair. Now my wife’s sister somehow looks nothing like her. Dyed blonde hair, 5’4″, a bit chubby and fake double D’s.
We’ve all spent quite a bit of time together over the course of the 4 years we’ve been together but I didn’t know much about my wife’s sister and her husband’s relationship. Turns out he’s a bit of a deadbeat and doesn’t treat her very well. I on the other hand worship the ground my wife walks on, waiting for her to realize she’s too good for me.
We Did a Quickie on Her Friend’s Apartment While They Were Gone [MF]
[Belle](https://www.reddit.com/r/gonewildstories/comments/e9jh89/i_m_decided_to_help_my_ex_f_with_her_thesis/) and I were a few months in on our relationship. As most couples do, we talk about everything and anything. That’s one of the things I love about her; she’s very smart and you can have deep conversations with her about life in general. I loved talking with her so much that if we can’t be together during the day I would call her on her phone and talk for hours. We were a relatively new couple then and as much as we loved each other, we were incredible horny as well so topics eventually veered into sex. Nothing kinky, we would just end up having sex on the phone when things get too heated.
**Side note:** Belle and I were in our early 20’s. We’re 15 km. (9 mi.) apart and still living with our respective parents’ house. I work in an office in her town. That’s how we met.