Category: gonewildstories

The Night I Ca[m]e Inside of my Ex Girl[f]riend

I have a love-hate relationship with copious backstory/lead-up so I’ll try and thread the needle here.

The events of this story transpired on a night during the summer after I graduated high school, but I should back up a little first. From sophomore to senior year, I had dated a girl named Jenn. I loved Jenn. We had a fun and vibrant relationship that seemed like it would never end. Not too long after we began dating, we took each other’s virginities and proceeded to fuck constantly for the next 2 years. I had more sex in that time than any other 2-year span since. Trojan stock soared…but then it ended. I’ll spare you the gory details of why the relationship ended, but let’s just chalk it up to her suddenly wanting something else shortly after the start of senior year. High school shit. It wasn’t until we were done that I realized just how lucky I had been with respect to Jenn’s body. Imagine a volleyball player. Tall. Long, thick thighs. Flat stomach. Respectable breasts. Long blonde hair. But most of all, HUGE ass. I was absolutely obsessed with her ass. Still kind of enamored with it to be completely honest. Suffice it to say that we fucked doggy style a lot. I’d say Jenn’s celebrity doppelganger would be a tall, and even curvier Amber Heard. To this day, any time I see a woman with Jenn’s body type I can’t help but stare. Pavlov’s dog. Read more »

While He Sleeps [MF] [Cheating]

Hello, Reddit, or more specifically, gonewildstories. I have been a lurker for a while now, not really posting any comments or anything. Granted, I’ve never been much of a commenter to begin with, so that’s not much of a change. Laying out the prerequisite “didn’t happen recently”, I’ve been sitting on this tale for over two years, as it’s something that I am somewhat ashamed of, despite having been quite a fun romp. I do not remember this as perfectly as I would wish I did, so any dialogue will probably be paraphrased unless it was something that stands very clearly in my mind.

To set the stage for you, this all began through connections to my place of work, which stands as a rather large retail chain. I won’t name it, for obvious reasons, but it is easily one of the big ones throughout the US. Despite working in another department, I had found myself becoming friends with a number of cashiers, one of whom, we’ll call her Laura for the sake of identification, began to invite me over to her house. Read more »

[M]y Girlfriend’s Roommate (LONG)

This is my first story; there are more to come if there is any interest.

This story begins during my sophomore year of college. I attended a community college while living at home during my freshman year, but moved into the dorms of a local university during my sophomore year. I had been dating Casey for about a year at this point and she was about to move into a new apartment with a high school friend, Alex.

I was a year older than both girls. I had taken a year off between high school and college, so I was 20 and both girls were 19. Casey was a brunette with brown eyes, about 5’5″ and a little on the curvy side, very cute with large C/small D cup boobs. She was a lot of fun, but could be very hot-tempered, which we shall see later in the story. Casey was attending cosmetology school, which started a bit later than my college courses.

Alex was blonde haired, blue-eyed and tan, about 5’7″ and athletic. She was your typical hot college age girl, a little full of herself but for good reason. She had a great body and large B to small C cup breasts. Alex decided to quit school after a year of college and was waiting tables at an upscale restaurant. Read more »

Surprising daddy with a [f]uck in the park

Warning: this is a loooong post and the first bit is the backstory.

So this whole encounter started with this craigslist posting I made:
> I really want to try a kind of anonymous/exhibitionist encounter. Basically the idea is we’d pick a specific place in a park (I was thinking local-park-name) where we’d agree to meet, like a bench or a landmark. You would get there first and tell me what you’re wearing so I know what to look for. I would be anonymous though aside from maybe sending body pics. You’d only know it’s me when I straddle you on the bench and kiss you. Just to be a tease I might jog by once or twice so you don’t even have a clue. After we meet and make out a bit I’d want to go back to my car (hatchback with tinted windows) where I’d let you shove your throbbing cock in me. I’d prefer that you be older and chubby/fat (I’m not completely against fit guys but the idea of me being in my workout clothes jogging around and then letting a chubby older man fuck me really sounds good). Without giving too much away: I’m fairly short and in good shape. If that sounds good shoot me an email, totally open to thoughts or suggestions for other anon/exhibition type stuff! Read more »

[MF] Getting what I want from a good wife

The curse of pregnancy is how big and beautiful her tits will become, but also too sensitive for me to really enjoy.

My wife is just about 5 months pregnant ([previous story](https://www.reddit.com/r/gonewildstories/comments/6gsflb/mf_making_my_wife_comfortable/)), which means she has those big amazing tits. Her normal chest is a 34D, and now those aren’t even close to fitting.

With the summer heat going, she spends most of the morning walking around in her panties, only dressing at the last possible moment. This past Sunday, as we are getting ready to leave the house, I come up behind her and lightly squeeze, while whispering in her ear how fucking sexy she is.

She giggles and tries to get away, but one hand is already going down her big belly, into her panties. Because she can’t really see past her stomach too well, she’s grown a nice little bush. My fingers play run through her hair, before going further. The tip of my middle finger just separates her lips, and she’s wet. Something about being pregnant makes her amazing wet at the smallest things.

Her hands brace against the dresser, and she starts breathing heavy as I slide my finger into her, with my other hand lightly playing with her nipple. Read more »

[F]ucking my favorite bartender

There’s this bar in my neighborhood that I like either starting or ending my night at. It’s not a dive or really high class — it’s just a cool bar with really awesome bartenders. I’ve become pretty friendly with some of the regulars and bartenders, and while it’s one of my favorite places for a convenient hookup, I usually keep it “professional” with the bartenders and the guys I see there all the time.

And I think we can tell where this is going.

Dean is my favorite bartender. 6’2, handsome, scruffy beard, tatted up from head to toe. He’s 29 and in an on-again, off-again relationship with a girl named Bethany. She loves a rugged guy as much as I do, obviously, but she hates a bartender’s hours/lifestyle.

Anyway, it was 9ish on a Thursday. Dean had been feeding me high-octane vodka sodas for the past 2 hours. He asked if I wanted to check out with him since he was getting off soon. I said yes, and of course, the bill was about half of what it should be. Then he asked me if I was done for the night or if I wanted to have a drink with him at a bar down the street. This was not unusual — I’ve hung out with the bartenders before, but usually as a group. Again I said yes. The drinking continued. Read more »

[MT] Some kinky cum swapping & frozen loads w/my college trans-girlfriend Meg. [kink]

You guys gave me such good feedback on my first post, so I thought I’d post one more. It’s a bit kinkier than last time, but what the hell.

So I dated a transwoman in college named Meg, and as I mentioned in the last story, and our first time doing anything sexual together, we 69’d, came in each other’s mouths, and cum swapped our loads.

We quickly got pretty nasty, trying basically everything there was to do. We took turns fucking each other, giving each other handjobs in a public park, blowjobs in a public bathroom, and because neither of us are that big, we started using butt plugs sometimes. Whenever I think back to it, it’s a little surprising to me how quickly I went from 0 to 100. I had only had one sexual encounter with a cisgirl – just vanilla PIV, and now here I was, basically sucking the cum out of Meg’s dick every time we fooled around. We actually both came in each other’s mouths almost every time we messed around. Maybe because it was such a special part of our first time together, we both grew sort of addicted to it. Read more »

The Spa Weekend – [FF] Toy time.

I woke up to a dark room and the sound of singing coming from the bathroom. A smile still on my face, I slid my naked body across the crisp cool white sheets heading straight for the shower and the gorgeous woman singing.

Gliding the curtain back on the rod, our eyes meet and smiles stretched across both of our faces. She says, “Join me.” We wash each other thoroughly, soapy hands traveling all over each other’s bodies. Our lips meeting for kisses every now and then, just letting the moment and the hot water wash over us completely.

Not much is hotter to me than a wet, slick body – the water helps exemplify every curve and undulation of the figure. Completely turned on and ready to explore again, we both agreed to grab a toy or two from our bags. I grabbed a clit suction toy and a vibrator. She grabbed just a magic wand. We both faced each other excited and ready to explore.

Laughing and giggling like school girls, only wrapped in the tiny white resort towels that pulled against our full tits. We walked over to the king size bed, gave each other looks that said who is going first. Read more »

[FM] Till Next Time

I ran his doorbell, rested my face on the white round handle waiting, I was feeling a bit of melancholy as this would be the last meet for a while, but crashed the building door into a stranger. Oops.

He pops out of his place half naked, a big infectious smile on his face.

We chitchat for a while, complain about stress while I enjoy his eyes hungry on me.

I step closer with a dirty smile. He holds my chin high, and stares at me, smiling. I stare back with a submissive sincerity, but it’d be too much, I want a kiss. His fingers lock me down with a light grip. I tip my toes and barely peck his lips, whimpering. He pulls my face in, gives a devouring kiss or two, not enough.

He is already hard. *I want that in me*. I start grabbing and rubbing myself on him. “Hmm? What do you want?” I let out a small moan. “I want your cock… I want you to fuck me”. “I will…” he smirks, but not yet.” Read more »

[M]y petite MILF [F]orever. [Cheating] [pics]

A couple years ago I posted an ad online with my phone number a couple days before Valentine’s day looking for a FWB. Around midnight on Feb 13, I got a text from a woman saying she has been told she’s a vixen along with a face and clothed body pic. We started texting and agreed to meet the next afternoon at a local diner. She told me she had a boyfriend but that it was probably going to end soon as he had cheated on her.

Within 5 minutes of sitting down for coffee we decided we were ready to go, I left more cash than necessary at the table and we just walked out. I had looked up nearby hotels the night before in case this happened so I had her follow my car to the hotel a mile away. We checked in, and when we got to the room it was on!

Me: https://imgur.com/79EVL9P

Her Doppelganger: http://www.milfsgalls.com/allover30/e37866/12.jpg

She was about 4’11, 100 pounds or so, tanned skin (as in she tans too much), she was in her late 40s, but the body of a 20 year old, albeit with a few more wrinkles and stretch marks, a cute tight face, and longer brown and blonde streaked hair. Like you’d expect on a girl that likes to go out and have a good time/party. Read more »