[MF] This past weekend, I endulged an older friend in her mommy fantasy, and I’m still reeling.

For starters, I’m 29 and she’s 44. We’re both professional theatre actors and met in a play we were in together about a year ago. We’ll call her Erin.

We got to be pretty close. It was a small cast, and our characters kind of hated one another, so it was fun to fake bicker with her backstage, considering she’s one of the most genuinely sweet women I’ve ever met. She’s about 5’9”, long brown hair. Wouldn’t guess she was 44 in a million years. I’d say somewhere around 35. You could definitely tell she was a bit older than I am, but it wasn’t drastic. She’d aged well. She kept herself in shape, and I admit I caught myself checking her out on more than once occasion, but we had such a professional relationship, and she’s 6 years younger than my own mother, so I never thought much of it.

Fast forward to last weekend, about a year since we’d done that play together. One of our mutual friends who was in the play with us was doing a play at another theatre in town. She sent a group text to everyone in the old cast asking if we wanted to go see it. I was the only one who didn’t have concrete plans, and I figured it’d be fun to see her again. So I agreed to go.

[M] masturbating and edging for over an hour.

Last week I found my way to a video challenging the viewer to edge and masturbate for about half an hour. I decided to take on the challenge as I felt that when pleasuring myself I went about it too quickly. It was harder than I had expected, I repeatedly disobeyed the instructions to stop myself from finishing too early. But once the 30 minutes had elapsed, and I was allowed to cum, I felt great and more cum than usual amount came out too.

After that I did similar challenges everytime I masturbated, and I was getting better each time. Then tonight I decided to take it a huge step further and masturbate for three times as long. I slid my hands up and down my shaft obeying the instructions to go slow or fast, to edge or stop. As time went by it became harder and harder to go on and the slow strokes made me almost lose it just as much as the fast ones, and all of this before I was even a quarter way through the video. I became more and more sensitive and was almost in agony by the time I had reached the halfway mark. But still I managed to make it through an hour, and then there were only a dozen minutes left to go, not long ago that was the time I would usually last. Once those minutes had elapsed and I could finally release myself a wave of pure ecstasy washed over me and my chest became covered in my own hot cum. I sunk back into my chair relieved and euphoric with a smile on my face.

[M]y Fling with a Married Woman [F] Part 1

**Some Backstory**

First of all I’m not exactly proud to have had a fling with a married woman. I met her online when we were both in bad situations. We became close and developed strong feelings for each other. I love her to this day. When we first met I was unaware she was married before my feelings for her developed and by the time I found out I no longer cared. I wanted her and lusted for her. She lived far away though and so I never acted on it. That was until September of 2018.

**The Meetup**

For reason’s I won’t get into I was travelling around a bit. One of my pit stops happened to be a few hours out from her. She was nervous and I was nervous because we both agreed to meet up at my hostel. A few hours before arriving (when she was supposed to be leaving) I get a call from her. She doesn’t want to go through with it. I’m not gonna lie, I was fiendishly horny at this point. All I could think of was having her in my hostel and fucking her. So I told a lie. “Don’t worry. It’s not a big deal. We’ll meet up as friends. There is no pressure on anything more. I won’t push you…” This was a lie. I knew it and she knew it. We had been having phone sex for months and knew each one of our kinks. There was zero chance we weren’t going to fuck. She let her mind buy into it however and decided to venture out.

[MF] Came inside the cutest girl I’ve ever gone out with on the first date, after 3 straight hours of rough sex

I’m going to preface this by saying this definitely isn’t the wisest thing I’ve ever done, but it’s also the best sex I’ve ever had. This just happened tonight and my head is kind of spinning.

Me: 22, 5’11” 170lb muscular and bearded. Just got out of a 4 year long relationship, so I’ve literally never dated or had sex outside of this relationship as an adult before. I downloaded a bunch of dating apps last week and have around 70+ matches across all of them, so I’ve just been trying to learn how to get back on my feet and date again.

I matched with Elizabeth on Hinge and was instantly interested. She was by far the cutest girl I had matched with so far. She was a cosmetologist, had a really good sense of style, and we shared a mutual love for cats of all things. Off the top of my head, she looked like a cuter and younger version of [Stephanie Andujar](https://m.media-amazon.com/images/M/MV5BMjAzODYwNzktNTQ4ZC00NWU3LTg4NmUtMDZkOGM5ZTM3MmQwXkEyXkFqcGdeQXVyMTYwOTc0NDI@._V1_.jpg).

I quickly asked for her number and asked her out to some wine, which she enthusiastically agreed to.

[M]y first time with a t-girl

I’ve posted here before about how I lost my virginity and now I’d like to share my first time with a t-girl.

It was a pretty lonely time for me. I just finished up my post-grad program, about to start a new job, and I was bored as all my friends were already working.

I decided to go into backpage. I was looking at females first and just wasn’t convinced that any of them were real. So I go to the t-girl part and begin to look there out of curiosity. I find this nice looking filipina and was convinced that she would be the one that would rock my world.

I give a text and get the typical sweet reply. She gives me quotes and after I explain to her it’s my first time, she tells me to give her a call. I do and she said she wanted to assure me that I’ll be taken care of and that I have nothing to worry about. We agree upon a time and I make my way there.

[FF] A follow up with my (allegedly) straight friend

[First post](https://www.reddit.com/r/gonewildstories/comments/ax89vi/ff_helping_my_allegedly_straight_friend_after_a/)

So, after the night you all enjoyed hearing about so much, we cuddled some more and I spent the night in Chloes’s bed. No funny business took place and it was actually all quite sweet. Things were less awkward in the morning than they had any right to be. We each had a bit of a giggle and I eventually went back to my room and we went about our lives. We did text a *lot* more after that. She reaffirmed that she wasn’t gay or even bi but that doing stuff with girls just fell on that weird grey area. The one where she doesn’t *actually* enjoy it, but gets off on being forced to do it. At least, that’s what she thought but couldn’t be certain. We didn’t broach the subject again for some time and I figured that was that.

[MF] After a crappy end to my 2018, I decided to fuck my way around Asia. Part 2 – The Philippines

Read Part One here:

https://redd.it/axn4v0

Hallie contacted me that afternoon to let me know that she could take off that Thursday and Friday to join me. I was thrilled. I asked her if she was available afterwork to help me with the travel plans and she said she was.

I felt like a dick asking her, but I had to prepare and as gently as I possibly could, I asked her if she was going to charge me. She snickered and said if all we were doing was planning than no., I told her I was at least going to take her to dinner. She agreed.

At 7 PM she arrived and dressed a bit more casual this time. I asked where she wanted to eat, and she suggested a pizza place that she’s heard good things about, and it was less than a kilometer from my hotel. She suggested we get it delivered.

I turned on my laptop and got to work. Though I googled Coron during the day, Hallie showed me more pictures on the web, and it peaked my interest more. The sites on the island looked gorgeous, but what I really wanted to do was fuck Hallie in a secluded beach. Since we were planning the trip, I went ahead and mentioned this to her. She smiled and she told me of different options.

My first encounter with Marie [MF] Long

Hello everyone. I have been reading stories for a few years but have created a new account to start posting some of my stories from a few years ago.

Backstory follows. Skip to “THE NIGHT” for the actual action.

THE BACKSTORY

Marie…..oh Marie how you still haunt my dreams to this day. And for the life of me I can not figure out why. She was not the most gorgeous girl I had ever seen. Cute but not overly, and she annoyed the crap out of me a lot. But she and I had this strange sexual connection I don’t think I will ever have again. For years we kept swinging back into each others lives even if only for a blowjob in a random parking lot somewhere.

Marie was maybe 5’3” on a good day and 100lbs soaking wet. Smallest tits I had ever seen but her ass was perfect. Round and firm, just right for grabbing. She was a member of a sorority on campus, and with me being in a fraternity that is how we met.

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART FOUR)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART TWO](https://www.reddit.com/r/gonewildstories/comments/av44cl/mff_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART THREE](https://www.reddit.com/r/gonewildstories/comments/avv157/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

It’s been a little over a week since the last update with Olivia, and I’d like to tell you that this past week was filled with wild sex every single day, but unfortunately life gets in the way sometimes. Olivia is always busy and travels often for work (which is why she’s looking for a new job), so it can be difficult to connect sometimes. In the past 7 (8?) days, we’ve only been able to get together once, and sadly she had started her period.

She invited me down to her place to watch a few episodes of ‘Russian Doll’ on Netflix. I had already watched the series, but it was pretty good, so I didn’t mind watching it again with her. It was around 8 or 9 at night and she was dressed in a pair of pajama pants and a t-shirt that appeared to be over 100 years old. It had holes in it and was basically hanging off her shoulder for dear life. I made some smartass comment about it, and then she battled back with, “What about you? King of sweatpants over here,” she had a point. For some reason I think I’m Drake. I can’t get away with wearing sweatpants all the time.

[M]onday [F]unday

Me: F 26 yrs 5ft, 100lbs, petite but I gots a lil’ booty because I’m black.

BD: M 36 yrs 5’9, maybe 180, fairly muscular for his frame, a decade older than me, but also looked great for his age because black don’t crack. Gorgeous light brown skin, tattoos, juicy lips, dimples, and a snapback hat covering his milk dud head.

We ended up talking about our experiences with polyamory, and he explained that his recently decoupling was why he had just moved into a new place. I explained that my own journey with polyamory had a lot to do with why I was moving back to Texas and he lamented the fact that we had sooo little time together. The conversation was easy and we vibed nicely especially while conversing about our beliefs and past difficulties with polyamory.

I went to the bathroom and he paid for our drinks and his appetizer. We ended up traveling back to his place making a short detour to get beers and snacks. In the car we went more in depth about about kinks and things we liked and past experiences. As we drove he kept squeezing and kneading my thighs in the car. We arrived at his house, and he gave me a short tour of his home. Of most interest was the basement that he planned to make into a bitchin’ group play space.