My [F]irst DILF

I have a DILF fetish. This is a story from several years back of a one time encounter when I was 19.

He was a very handsome bald man, his tinder profile said he was 29 but later on he would tell me he’s actually 36 with three kids.

I forget how to conversation went down but I drove over to his neighborhood of the city and he met me outside and we walked back to his apartment. Almost as soon as we got inside, he made his move on me and I was hooked. He was perfectly aggressive where it was so hot, pinning me down and just using me and playing with my giant tits and rubbing my clit. He had ripped all my clothes off and threw me onto the couch, and started going to town eating my pussy.

I was soaked and moaning on the couch, and he licked his fingers before sliding two of them into me. He skillfully fingered me with such knowledge and passion, I couldn’t control my moaning and suddenly, for the first time with a man, I was squirting all over him. He loved it, and ate my pussy even more until I turned around to start sucking his dick. Just as I was getting into it, his phone rang with an emergency. We had to finish and quickly get dressed so he could go help with this situation, but I was still disappointed we hadn’t gotten to fuck.

[MFM]Watched my [F]riend take two cocks on New Year’s [exhibition] [cucking]

So long story short my friend Kate has been fucking me and another guy named John. After sharing her with John for awhile I’ve expressed interest in watching her with multiple partners and have watched her have sex with John in front of me. Over the new years holiday she decided to step it up a bit and have sex with John and another guy she met and invited me over to see it. This post is from that night.

Around 9pm New years I get a text from Kate telling me come over because she has a “surprise” for me. I get to her apartment and walk up the stairs with her. I open the door and John is sitting on the couch and other guy is there with him (We’ll call him Matt). Kate introduces him to me and pulls me into another room and gets right to business. She tells me “Sooo I know you’ve wanted to watch me with more men than just John so I’ve been trying to find someone to join us.. annnd I found Matt. He’s interested in sharing me with John and has done this sort of thing before.. is it okay if I have sex with them?” I tell her yes. She lights up and starts making out with me. We make out for a few minutes “Oh my god baby I can’t wait… You want me to go ahead and get started?” I tell her yes and she gets undressed. She rummages around in her underwear drawer and finds something sexy wear and picks out a frilly push up bra and thong. She changes and kisses me again. “You ready babe?” I tell her yes i’m ready.

Rainy NYC Night [MF]

**Rainy Night In the City**

Water dripped onto the elevator floor.  There was no helping it.  Both of them were soaked completely through.  All that could be done, was to head to the hotel room and change out of their wet clothes.  It was early March, the weather had been warming up, and they had decided to break the winter blues with a trip to the city for a weekend.  Neither one said it out loud, but both would be glad if it was snowing outside instead of the freezing rain that had been falling all day.  

They tried to make the most of it.  Sightseeing, walking around, a little shopping and a nice dinner.  The rain, however, was putting a damper on their plans, and souring the trip a bit.  An attempt to purchase an umbrella from a street vendor, resulted in the cheap, quickly broken umbrella in a trash can, and his wallet $20 lighter.  A bar they found gave them refuge for a bit, but after 11pm it started to become overcrowded, and they decided to head back to the hotel.  No cabs could be found, so they had to hoof it for a few blocks.

[MF] Story of my first ever one night stand with very petite 5’0″ 85 lbs Asian girl, i was not expecting her to finish me off this way..

2I had some decent interest in my first post her a few days back so figured this would be a fun story to tell, i had written this up a few days back but the title was not that relevant to the overall story and what the experience represented and my grammar etc was pretty bad so I’ve re-articulated everything this time round

I’ll start with a bit of backstory, start of last year I rocked up to a mates 26th bday about 2 hours late, it was a Saturday night, most people were either totally drunk or passed out with a few still left sober and just chatting, so i stuck with another couple i knew and we were just chillin in our corner and talking to others randomly when they came over for small talk

I noticed early on a very petite asian girl, she was probably 5’0 or maybe 4’11 and looked about 85lbs (she was indeed 85lbs as i discovered later down the track) she was wearing a big shirt with black leggings on, she didn’t really have much of a body, no boobs and legs were skinny, a few times she was reaching up towards the kitchen cupboard to get something and i peeked over as her shirt went up and revealed her ass

My year as an escort, and the time my best friend was a customer [FM] Part 4

[Part 1](https://www.reddit.com/r/gonewildstories/comments/adhjyt/my_year_as_an_escort_and_the_time_my_best_friend/)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/adssx3/my_year_as_an_escort_and_the_time_my_best_friend/)

[Part 3]
(https://www.reddit.com/r/gonewildstories/comments/ag7yr7/my_year_as_an_escort_and_the_time_my_best_friend/)

With a gentle touch, I opened the fridge, and reached into the freezer to pull out an ice cube. Facing the hotel room mirror, I ran the ice over my nipples, feeling them grow hard and sensitive.

Then I stuck a hand into the jar of nutella I’d brought, and scooped out a handful to lather on my breasts.

I checked myself out in the mirror. Underneath the layer of chocolate spread, you could see the faint outline of my supple, shapely breasts, with small, brown nipples just poking out of the surface of chocolate goo.

My eyes traced down my flat stomach towards my pelvic area, where my freshly waxed pussy awaited its treatment. With a sigh, I scooped another handful of nutella and began lathering it over my pubic area, careful to avoid my actual vaginal opening.

When my pelvic area had been sufficiently lathered in chocolate hazelnut spread, I tiptoed to the bedroom, and softly opened the door. “Baby.” I crooned. “I’m ready for you.”

[MF] Sex with the younger(18) girl

To start off I’ll describe myself. I’m 28, 6’3, muscular fat body type (I love Taco Bell), and I’ve been told I’m good looking a few times.

I had been broken up from a 10 yr relationship about 6 months when I decided I had to start putting myself out there. I use bars, instagram, and various dating apps to meet girls usually. Every once in a while, I’ll go on the whisper app just to see what’s up in the area.

Maria had been posting some provocative selfies over the past few weeks, so I decided to send her a msg and see what was up. We got to talking for a while and kind of just clicked so the conversation flowed easy. Then we moved to Snapchat where the pics started flowing. She would post parts of her body, nude and clothed, in her story but only I could see it.

Let me describe Maria now. She is between 5’ to 5’4, a little thick but it’s in all the right places, and she has a piercing in her bottom lip and nipples. She’s Mexican, light skin and really sexy. Her tits are 36DDD and her ass is just as good.

[M] With Her [F] #1

It was a stormy day, school had just gotten out, my parents weren’t available to pick me up. My girlfriend had just left to go home, she’s the love of my life, I love her with all my heart and as does she. I know she’s the one for me, we’ve done basically everything together, we want to grow old and live out our life with one another. But nothing is going to prepare me for what’s about to happen. I went over to ask my friend if her boyfriend could give me a ride home along with them, her boyfriend had just gotten done with baseball but had to go to the weight room so he asked her to give me a ride, they both could drive obviously. I had some hesitation in the matter since I used to like her and my girlfriend would get upset when I was with her. She was very pretty alright, and my heart always races when I’m next to her. I always had some thought that she might have liked me too. Eventually we ended up going to the car and went off to my house. I told her the directions to my house, the car ride was pretty silent, she didn’t put on the radio which was pretty weird since most people do. We were then right outside of my house parked on the street. The roads were slippery which made it hard for her to drive. It was so rainy that the pitter patter on the windshield made it seem like hail and fogged up the streets. I said my goodbyes and thank you for the ride and I looked over to her. Those eyes. Those eyes stared right at me and I stared back. For a second it seemed like she implied something and I hesitated for a few seconds. Then, inch by inch our lips are drawn to each other like a positive and negative atom. I kiss her and she. She kisses back, her lips are soft and warm. The taste, I can’t even describe the taste of her lips, so sweet. That’s it. I decided that we should’ve stopped, we were both faithful to our partners but this, this didn’t seem like cheating. Was it? We decided never to tell them and went onwards, I reached for the door handle but she…she locked it?! I looked back over to her with a grin on her face. Such a naughty girl I thought but it didn’t feel right for me. My heart was pounding out of its chest as I looked at her, my mind was racing on all the things that could happen and eventually I reached over to her cheeks and went in with another kiss, a long and passionate one, one only lovers would do. Suddenly my hands start to wander, I touch her back as my hands then wander to her firm boobs and then down to her back again, such a wonderful arch there is. Down to her ass, and I fondle it for I am an ass man myself. She tells me to go to the back of the car, and I do as I crawl over from the passenger seat. Sitting there, she climbs back as well, and sits right on top of me, right on top of my huge hard mound that’s forming from my sweats. She realizes and I can feel the warmth of her insides emitting onto my head. She starts to grind on me a bit. We make out some more and I fondle her body, she lets out a soft moan, and as she lifts her head, in that split second, I kiss her neck long and passionately like how I would my own girl. We continue this for a while then she strips off her flannel and shirt and it’s just her bra now. I stare in amazement and she looks confused at me, I was wondering what was going to happen next, but I already knew where this was heading. I do the same and remove my jacket and shirt. I stare at her, such a beautiful woman that I have in my hands, that I was  able to do anything with, she was my crush and I still felt for her and now we were finally here, where I always wanted to be, with her warm body next to mine. I didn’t hesitate to tell her to undress even more. The first thing she does is to take off her boots and socks. Her feet, oh how small and precious they were, soft, like a velvet chair, and just in the right proportions to make them all have a nice arch all around. She takes off her leggings, she’s just in her bra and underwear now. I help her undo her bra. There they are, her nice firm tits, beautiful and plumpl, and her nipples, they were perfect and hard from the stimulation I had made for her. Her arreolas weren’t small or big but perfect. She has the perfect body, her hair and face were perfect, such length and curls to her amazing long and natural hair. I help her take off her underwear. And there it is, the insides of her that I’ve wanted to feel ever since I caught feelings for her. She shaves, so that’s a plus for me, her vagina is perfect for me, no folds or flaps. Just an opening and some beautiful labias. I take off my sweats to unveil my massive rod upon her. She’s not used to something this big she said. She says that I’m much bigger than her boyfriend. I’m pleased to hear that, it turns me on, and I get harder for her. I decide to try and slip it in, I lift her up and onto me. My head feels the wetness and warmth that’s been created, it doesn’t slip in easily like what I’m used to. She’s tight. Very tight. And since I’m uncircumcised, I know this is gonna hurt. I hold my dick while it inches its way in and in, and she moans and lets out a loud one that fills up the car, I keep pushing and pushing and it hurts me, I’ve bled while trying to do this but she’s wet like nothing else and finally I’m there. Now I’m in, all of it. It hurts her and I say sorry. She tells me that it’s okay and then she rides me, up and down she goes, and my dick, the sensation of her walls tugging at my skin and rubbing my head is so strong that it makes me want to cum. I hold back, we go on and on for what feels like an eternity. She tires out and I grab her back and ass, and switch positions. We’re in a missionary form now and now I don’t hold back as I fuck her, I fuck her real good, my dick goes in and out of her vagina and I try to speed it up to make her feel good. Her face tenses up andher brows raise and her eyes roll from the immense pleasure I’m causing for her. Her legs squeeze around my hips. Her legs are so soft and crossing behind me, her tiny feet and toes are curling behind me. Her moans are so sensational to my ears, I analyze her body while I’m fucking her. Watching my dick sliding in and out of her vagina pleases me. I put my thumb over to unveil her clit, I then rub her clit up and down with my thumb. With this sensation she screams and moans from the sudden burst of pleasure that has exploded from her body and is now traveling throughout the rest of her body. I stop and then grab her legs and put them over my shoulders and I push deeper and harder and faster than last time. She moans and screams again. She knows that this is what real sex is. Finally, with more constant moaning and staggered breaths that fill up the car, she cums as her entire body seems to have an orgasm as she’s shaking all over, I however, I haven’t came yet, and I keep going, I fuck and fuck. She lays there with her eyes rolled back scratching her nails on my back with her legs folded around me. My dick is pulsing and I keep pushing, she cums again within seconds of the first one. She lets out a groany “oh my gooooood,” this turns me on even more and I push with one last effort which almost made me cum. It’s a good thing I didn’t. She sighs and tells me if I came. I tell her that I haven’t and I slowly pull out and push in again. She moans, this time, with a slow and hollow moan, her mouth is just open and her eyes closed from the pleasure that’s overtaking her. I speed up and I speed up until I feel it. I keep going, trying not to cum and I see her do it again. Her eyes rolling up to where I only see white and her legs tensing around me. I try to pull out. But her legs. Her legs stop me. My mind is racing from the pleasure, the excitement of finally being able to fuck her, and to this moment to where I might have gotten her pregnant. With just enough force, my body is released from her insides and there it is, my cum. It’s being released onto her stomach as she sighs again. She says that there was so much that came out and how warm and hot it felt on her stomach. We finally have a chance to catch our breath and she says  “Wow, that was….that was amazing.” I look at her whole body gazing at what I might never be able to see ever again. “Yes, yes it was” I finally reply.  She tells me that she’s not used to such a big dick and I tell her that her pussy is the tightest I’ve felt as I stroke her pussy one last time with my fingers, so wet still and she shakes at the touch of it and her legs raise and extend. It’s exciting me. I ask her if we could have a mini photoshoot since I’d never be able to see her beautiful body ever again. She agrees and she also says that this isn’t a once in a lifetime opportunity, and by that I wasn’t sure what it meant but I took it as that this would happen again, I don’t know when, or where, but it would. I take my phone out and start taking the pictures, I ask her to get into all these wonderful poses that excite me. She shows me her soles and I wish I would’ve finished on them. I love soles, hers were no different, so soft and fragile and smooth. I take the pictures of her vagina, her beautiful curvy ass, her feet, her legs, I tell her to spread her legs and pussy, she does as I say, I take more pictures. I started to wonder, how does her pussy taste? I go in for a sniff, it smells beautiful, my tongue goes into her insides for a second as she shakes again. It tastes beautiful. If beautiful was a taste at all. She asks what I’m doing, I tell her that I was curious of what she tastes like. We continue with the pictures and poses. Her tits and clit are wonderfully smooth. I finish with my photos and I tell her thank you for this wonderful time, she says “you’re welcome,” I reach over to hug her. We then kiss and make out some more but her wonderful lips make me not want to leave but I know I have to, we’ve been here for too long that it might have made our partners suspicious, especially her boyfriend. I put on my clothes as does she. I kiss her goodbye and run into my house where it’s warm and as I’m going up the stairs, she then texts me with the words “Until next time lover boy ;).”

[F]ucking [M]y younger coworker for the second time

Jump to *-*-* if you want to skip the backstory and get right to the action.

This was the second time I fucked my 12-year younger work subordinate ([Read the first time here if you’re interested](https://www.reddit.com/r/gonewildstories/comments/amzh1x/fm_turning_my_much_younger_work_subordinate_into/)). I’m sharing because this time was completely different to the first.

After the first time he had choked me out and owned my ass so completely in the backseat of his car, I honestly thought that was gonna be it – a one-time thing, and I was completely fine with that even though it was amazing sex. I was just happy I got to live out my fantasy of fucking him in the first place after he had initially rejected my offer.

A couple of weeks had passed since that first time. The station had another event. Our group of friends usually made a habit of having an “after party” at one of our houses after events and it was completely normal for some people to sleep over, especially if they drank. I was really tired after a long day and wanted to get the best mattress to myself, so I called it a night early and called dibs on the room I knew had the best mattress in it, even though the mattress was actually on the floor instead of on a bed frame. I passed out cold.

My [F] threesome experience [MFF] -Part one [Long]

Hey all! This is my first time posting to Reddit! I have been a long time lurker, and have been waiting for the moment where I would have a story to share. And now I have many. Stay tuned for Part 2 and Part 3.

I have always had a fantasy of having a threesome. Since I knew what a threesome was. I have been openly bisexual for a long time, and the idea of having sex with a male and a female at the same time seemed like a very fun time. Sex in general is one of the most fun things that people can do. Isn’t it logical that the more people there is, the better time it could be? I needed to try this out. I was having an casual fling with a girl named Katie, and she was the perfect partner for a threesome. We had talked about it before, and felt confident we could find a guy to join. I messaged her one day after we had hooked up, asking her if she was still interested in finding a third. Since a threesome was also a fantasy of Katie’s, she happily agreed that it is a great idea. She has a couple of guy friends who she is casual with, and would likely agree to the idea. She texted them right away, and both replied that they would be interested at some point if we could make it work. These guys names are Jake, and Mike. Jake is the first one we are going to talk about in the threesome stories, as he was the first one to join. But Mike got his chance too.