Category: gonewildstories

I [f] fucked my boss’ boyfriend [m] during a summer internship in college

Hey r/gonewildstories, Rachel here again with another story for you guys! Sorry for the long wait in between new stories but I’ve been really busy lately and haven’t been on reddit.

For those who haven’t seen my other stories, here’s a quick description of myself: I’m 5’6”, with auburn hair, some slight freckles, hazel eyes, 32C boobs and a pretty nice butt if I do say so myself! I try to keep in good shape with running and swimming so, at risk of sounding egotistical, I have a really good body. I’m 24 years old, although this story takes place a few years ago when I was still in college. Alright, let’s get into it!

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The teacher [F]antasy

This is a repost, edited for clarity.
So back in high school (about 2 years ago now) there was this hot teacher, well call Adam. Adam was pretty much every girls fantasy. They’d go into his class and just talk with him, or take extra long to drop off papers. They’d want his class just to look at him. He was also 27, while I was 18. I didn’t think he was very good looking until the second semester of my senior year. When that happened, it’s like he noticed me as well.
Once, walking to my car after school one day I caught him checking me out. If we saw each other in the hallways we’d smile. I was in yearbook and had to interview people for my page, I ended up in his classroom, and no exaggeration he acted like he only noticed me (I was in there with 2 other people) He only talked to me and kept looking at me. I was so nervous I didn’t say a word.
Anyways, cut to graduation where were in lines to rehearse. My line ended up being right next to his. I was at the back, he was at the back, again he checked me out. Coincidentally, he also ended up walking next to me on the way to the parking lot as well after that day. But, keep in mind we weren’t talking in anyway at this point.
About a month after graduation my friend told me to add Adam on Facebook. I did, he accepted pretty much right away. Nothing happened for a while until a drunken Friday night. I was scrolling through my feed, champagne drunk & I decided to check Adam out. I liked a few of his pics, he liked a few of mine, back and forth back and forth. Then he slid into my DMs with that sexual sly face emoji and it went bananas from there.
We talked all day everyday, about everything. His likes, my likes, our dislikes, he was definitely trying to flirt with me and show he wanted me. I, at first, was not into it. I didn’t think he’d want anything to do with me if he knew who i actually was. After a few days I brought up if he actually knew who I was (a student) and he did, and he admitted to checking me out. So that was that, no mystery.
A few days after that he invited me to his house. I was against it at first but figured fuck it, I’m legal, he knows who I am, I’ll go for it. I didn’t think anything would happen, It was a Wednesday night, he had school the next day, it was already 8 when I got there. I really thought we would just talk and get to know each other in person. Keep in mind, before him I only had one long term boyfriend and sexual partner. I was naive. But lo and behold, we actually did end up doing the deed. We fucked, sucked and came. I thought it was amazing, his dick was huge, his head game was awesome. I was impressed. What was I supposed to say, a guy 9 years older than me had to have more experience and actually know what he was doing right? Wrong. At least I figured that out after getting more experience. Having sex with him was like having a hot, thick rod connected to a dummy pounding you. No other stimulation.
We ended up “dating” from there. I say that because it was basically just me going to his house, us talking for hours and having sex. He took me on a few dates, to a concert and out to eat. But I never met anyone in his life, he never met anyone to me. But he did teach me about pouring cans of beer into plastic cups and drinking and driving.
I only sucked him off once because he was so big (again, no experience) I know I was terrible. I do get very, very wet and he loved that, but he was so big I couldn’t really get set enough. He never made me cum, and he lasted for either 2 mins or an hour. But now with more experience, I realize he was actually pretty bad. Between his jack rabbit anger sex or his intense eye contact slow sex, it was probably actually a 3/10 compared to the 11/10 I thought.
I stayed the night a lot. We’d cuddle pretty much the whole night, until I got hot or he turned over. We’d have sex in the middle of the night after I’d grind on him when I knew he was half awake or when he’d start rubbing me and I’d wake up to it. He was pretty big (at least 9 inches and very girthy) so he cock was hard to ignore) That was good sex, the sleepy just need to cum but this is so hot sex.
After a while I realized he was actually very weird, immature for being so old, and also a teacher dealing with kids everyday. I’m not sure what it came down to, I think his last breakup really fucked with him. I think he had daddy issues. Or maybe I was just a rebound and he didn’t care about anything. It ended pretty soon after it started to get to the lines of what are we, what are we doing. After about 3 months he just stopped replying to me the day after I went to one of his football games (he was a coach). I texted him a few weeks later and he said he was great and happy. Maybe I was a lapse in judgment, maybe I was a rebound. All I do know is I wasn’t his only student fling.

[FM] Mutual Masturbation with my childhood friend

So I fucked my childhood friend over the summer. You can read about that [here](https://www.reddit.com/r/gonewildstories/comments/7blkrp/fm_fucked_my_childhood_friend/).

Since we go to the same college, we’ve fooled around a lot more since then. One day I was over at his place, lounging on his bed. I was wearing a cropped hoodie and booty shorts while he wore just boxers.

I’ve caught him jerking off more times than I can remember and have always been turned on by the thought of him stroking his cock, moaning, and just getting off in front of me.

“Show me what you like” I say as my eyes drift to his growing bulge. He starts rubbing himself over his boxers, the outline of his hardening cock making my pussy swell. I watch with intent as he releases his cock and starts stroking, letting out a moan as I lick my lips. God he looked so fucking sexy, gripping his cock tightly, watching me as my hand drifts to my pussy. Read more »

[MF] Milfs ass popped out durring sex.

I’m working in a company for some years, almost from day1 a hot milf (12 yrs. older) draws my attention and she was drawn to me, at least I felt it. Could’nt really confirm it, since we only met at work and working in different departments. Read more »

[MF] Becoming My Landlord’s Pet (Part Fourteen)

My tongue flicked up and down on the asshole presented before me, aided by Michelle’s hand spreading the asscheeks of this stranger, and pushing my head deeper.

Emboldened by the moans coming from the girl in front of me, and curious as to how tight her belt may be, I opted to slip my tongue south and see if I could get a taste of what I imagine to be her dripping pussy.

Instead, my tongue tasted metal and a set of balls.

I let out an audible “ohhh”, that was half whimper and half human. The first time I ever remotely slipped out of puppy headspace as my lips now kissed a set of smooth testicles, framed by the metal cockring. I slowed down. Processing what was before me was so overwhelming that I ceased being able to think and act. The scents and sounds and breasts were all female, so this *puppy* before me having a locked cock was such an unexpected development I had to take a second to realize there was what I imagined to be a gorgeous, thin, and kinky trans female puppy sister with me.

“You two are mischievous, aren’t you?” Read more »

How my current FWB came to be. [MF]

Cleaned up story a bit :)

I’m an Asian, 39 years old and 5 foot 2” and 120 pounds..

This was during the summer at a beach resort

Hubby and I were at a company retreat and he (Ron) was my coworker at the time and was staying in the room next door, but the balconies adjoined. Ron poked his head over one morning and said he heard us last night (having sex). I was still in my nighty in bed and a little surprised when he poked his head over. Hubby invited him in and he sat on the bed next to me wearing just his shorts. We talked some and then he came back to talking about hearing us. I got a little excited about him hearing us but didn’t say anything. Ron said how he had always thought about what it would be like to see me unclothed. Hubby teased him some and pulled down the covers a little and rubbed me over my nighty. I was taken back some, but in the moment seeing how excited Ron got made me a little excited as well. Hubby could also tell he got excited and looked at me and went a little further and pulled all the covers off. I didn’t say anything but hubby could tell I was enjoying it. Hubby was also taking some pics with his phone then asked Ron if he wanted to see more and grinned at me. He then started to pull up my nighty exposing my bare ass and rubbing me. Before I knew it I had my nighty off and was there naked while hubby was rubbing all over my body. It seemed crazy at the time to be completely naked laying there in front of my co-worker. Read more »

Night long sex with the girl in the dress [MF]

I met this girl a little while ago back at a family gathering. It’s not incest shit lmfao…she’s my aunts niece, no relation. We hit it off right away but didn’t get together until a few nights ago. After a night out, skipping the boring details, she came back to my apartment and we went up to my room…

She unzipped my fly, pulled out my penis and put it in her mouth. She was still wearing her dress. I watched her long eyelashes and curled tips move as I grew bigger in her mouth. Her bracelets making a sound against each other. Wrapping around me with her long and soft tongue, I moaned I was about to cum.

As soon as I said that she stopped. She moved away and began to undress me. Taking off my shirt, pants, tie, underwear, everything. She made me lie down on the bed, her clothes still on. Sitting on the bed she took my hand and guided it to her vagina. She wasn’t wearing any panties. I felt the warmth of her vagina. As she shoved my fingers in, it was deep, warm and very wet. Read more »

The Hotwife [MF][short]

Inspired by pictures by /u/littlelambLucy; links in comments.

My cock always throbs so hard when I watch her getting ready for a date. She knows it, of course, and loves to tease. We’ve been doing this a long time now – I’ve lost count of the number of evenings I’ve been home alone, waiting for her – but every time is still just as exciting. Our agreement means that I don’t touch myself until she is home and telling me all about it – a condition which I am only too eager to accept.

Tonight’s guy requested a schoolgirl theme, and keen not to disappoint she went and bought the shortest skirt I’ve ever seen. She put it on the instant she got home, even though the date wasn’t for a few hours yet, and has been showing me glimpses of her perfect ass underneath the whole time. It’s so hard to resist grabbing, but she likes to keep herself for her dates, so by the time she left I was an aching mess. Read more »

Black Friday action with a co-worker [MF] [long]

For the past few months I’ve been working as an assistant manager at a retail clothing store in the mall. I won’t say which store, but it caters to teenagers and twenty-somethings and has obnoxiously large photospreads of waify models falling all over one another on the walls, and a too-loud playlist heavy on dubstep with some neo-folk sprinkled in for good measure. Working there is usually boring as hell and the pay sucks, but at least all my female co-workers are really hot.

Until very recently they were also way off-limits, not only because we have a draconian personnel manual that makes dating a co-worker about as fun as being a crackhead on parole, but because I genuinely wanted to be professional. Most of these girls had enough creeps in their lives, including the preening college jerks who came in bunches and the middle-aged men who sauntered through, sometimes with adolescent daughters and sometimes alone, always spending more time browsing the merchants rather than the merchandise. Read more »

Staying late for work[MF][Cheating]

So I had been talking to a co workers wife for some time. We had started talking at a work gathering, and had ended up with each others cell phone numbers that night. Fast forward about three weeks…
We agreed we would tell our significant others that we were working late, and met up near one of the stores on base(We were both Marines). She climbed into my jeep, and we headed for the beach on base. Once there, I put the jeep into four wheel drive, and took one of the Dune sand roads to a little hidden parking spot on the water(land side), and surrounded by trees. I had fished here before, and knew that you could, and usually did, go all day without anyone bothering you. The entire drive there we made small talk, nor really letting the conversation get too dirty.
Once parked, we moved to the back seat of the Jeep and kept talking. After a few minutes, she looked at me and said “So, why are our clothes still on?” That was all I needed to hear, to quickly take my boots, pants, and top(s) off. She did the same, finishing before me, and while I was taking my undershirt off(last article of clothing) she reached over, and grabbed my already hard shaft and started stroking.
Once I joined her being naked, she straddled my lap, and started making out. I’m 6’1, and about 190 pounds at this point. She was about 5’4, maybe 110 pounds. We are Marines, so we were both very fit. She took this opportunity to grind her pussy into my shaft, getting noticeably wetter with every slide. Her perky B cup breasts were right in my face, and I had no problem slowly licking, then sucking, then nibbling on her nipples, as she brought her hips up high, and finally lowered herself down onto me. She rocked her hips back and forth, and I could feel her stretching to take my length. She was so tight and wet and withing a few minutes, I felt her lips quiver, and her torso start to tighten as she came. She didn’t stop, only slowed down, and kept grinding. After another 5 or so minutes, she said she wanted me to bend her over, and, seeing there being no way to do it in the back of the Jeep, I opened the door, and slid out, pulling her out, then bending her over, so her torso was in the back seat, and started fucking her there. Her hips popping back was such a tight, and massaging position to my shaft, that after a few minutes, I already felt myself swelling, getting ready to cum. I said I was about to cum, and she looked back at me, smiled, and said “Deep, fill me with your cum Sergeant.” A few thrusts later, and I slammed my hips against her ass, and let out a large, long load, filling her squirt after squirt,until I stopped throbbing. We took a minute to catch our breath, then got our uniforms back on, and started to head back to the parking lot she left her car. On the way there, still on the back roads between the beach and main side, she leaned over, and pulled me out, sucking all my cum and her pussy juices off of my shaft. We got to the parking lot, shared a quick kiss, then she got in her car and left.
We carried on a affair for about 9 months, before stopping seeing each other. A year later, we started again for a few months, then stopped for good. I still talk to her a few times a week, but she is happily married now.